Themed collection Total synthesis in OBC

154 items - Showing page 1 of 3
Review Article

Total synthesis of bioactive tetracyclic norditerpene dilactones

Tetracyclic norditerpene dilactones are an important class of terpenoids that have been isolated from both terrestrial and marine sources, typically from Podocarpus plants and from filamentous fungi.

Graphical abstract: Total synthesis of bioactive tetracyclic norditerpene dilactones
From the themed collection: Total synthesis in OBC
Review Article

Total synthesis of the pseudoindoxyl class of natural products

In this review, we highlight the completed as well as the formal total synthesis of the spiro-pseudoindoxyl natural products, with a focus on methodologies developed for this key structural unit, challenges associated at the strategy level and the a future perspective.

Graphical abstract: Total synthesis of the pseudoindoxyl class of natural products
From the themed collection: Total synthesis in OBC
Review Article

The biology and total syntheses of bisbenzylisoquinoline alkaloids

This mini-review provides a concise overview of the biosynthetic pathway and pharmacology of bisbenzylisoquinoline alkaloid (bisBIA) natural products.

Graphical abstract: The biology and total syntheses of bisbenzylisoquinoline alkaloids
From the themed collection: Total synthesis in OBC
Review Article

Recent reports on the synthesis of γ-butenolide, γ-alkylidenebutenolide frameworks, and related natural products

This review focusses on synthetic strategies for γ-butenolides from 2010 to 2020 with an emphasis on γ-alkylidenebutenolides and related molecules. Metal-mediated catalytic transformation and organocatalysis are the two main reaction partners that were widely used.

Graphical abstract: Recent reports on the synthesis of γ-butenolide, γ-alkylidenebutenolide frameworks, and related natural products
From the themed collection: Total synthesis in OBC
Review Article

Contemporary advancements in the semi-synthesis of bioactive terpenoids and steroids

This review discusses the reemergence of semi-synthesis as an efficient approach to prepare bioactive complex terpenoids and steroids.

Graphical abstract: Contemporary advancements in the semi-synthesis of bioactive terpenoids and steroids
From the themed collection: Total synthesis in OBC
Review Article

Nonbiomimetic total synthesis of indole alkaloids using alkyne-based strategies

Significance of nonbiomimetic natural product synthesis and nonbiomimetic total syntheses of indole alkaloids based on the construction of core structures using alkyne reactions are summarized in this review.

Graphical abstract: Nonbiomimetic total synthesis of indole alkaloids using alkyne-based strategies
From the themed collection: Total synthesis in OBC
Review Article

Stereoselective syntheses and biological activities of E-series resolvins

Total syntheses of E-series resolvins are reviewed, along with the most significant bioactions of the E-series resolvins.

Graphical abstract: Stereoselective syntheses and biological activities of E-series resolvins
From the themed collection: Total synthesis in OBC
Review Article

Recent advances in the synthesis of plakortin-type polyketides

The recent progress in the synthesis of plakortin-type polyketides is summarized, with an emphasis on the key elements enabling rapid assembly of the polycyclic cores of chased targets.

Graphical abstract: Recent advances in the synthesis of plakortin-type polyketides
From the themed collection: Total synthesis in OBC
Review Article

Emergence of 2,3,5-trisubstituted tetrahydrofuran natural products and their synthesis

Diverse syntheses of emerging 2,3,5-trisubstituted-THF natural products are reviewed encompassing strategies based on catalytic methods, cascade reactions and rearrangements.

Graphical abstract: Emergence of 2,3,5-trisubstituted tetrahydrofuran natural products and their synthesis
From the themed collection: Total synthesis in OBC
Review Article

Total synthesis of natural products using photocycloaddition reactions of arenes

The photocycloaddition reaction of benzene with alkenes has become a significant approach for organic chemists and thus has been frequently utilized as a key step in the total synthesis of natural products.

Graphical abstract: Total synthesis of natural products using photocycloaddition reactions of arenes
From the themed collection: Total synthesis in OBC
Review Article

Strategies for the construction of γ-spirocyclic butenolides in natural product synthesis

This review describes the stereoselective synthesis of a γ-spirocyclic containing natural products or model compounds showing phytotoxic, antibiotic, anti-inflammatory, antiviral, antimicrobial, cytotoxic, and antitumor activities.

Graphical abstract: Strategies for the construction of γ-spirocyclic butenolides in natural product synthesis
From the themed collection: Total synthesis in OBC
Review Article

Palladium-catalyzed asymmetric dearomative cyclization in natural product synthesis

This review discusses palladium-catalyzed asymmetric dearomative cyclization, which is invaluable for producing enantioenriched materials, for complex natural product synthesis.

Graphical abstract: Palladium-catalyzed asymmetric dearomative cyclization in natural product synthesis
From the themed collection: Total synthesis in OBC
Review Article

Synthetic approaches towards cortistatins: evolution and progress through its ages

With an exhaustive coverage of all the synthetic approaches towards cortistatins, this review serves to assemble most of the avenues which have been employed to conquer this complex steroidal alkaloid architecture.

Graphical abstract: Synthetic approaches towards cortistatins: evolution and progress through its ages
From the themed collection: Total synthesis in OBC
Review Article

Asymmetric copper-catalyzed conjugate additions of organometallic reagents in the syntheses of natural compounds and pharmaceuticals

Stereoselective copper-catalyzed conjugate additions of organometallic reagents serve as a versatile tool in the total syntheses of diverse natural compounds and pharmaceutical agents.

Graphical abstract: Asymmetric copper-catalyzed conjugate additions of organometallic reagents in the syntheses of natural compounds and pharmaceuticals
From the themed collection: Catalysis & biocatalysis in OBC
Open Access Review Article

Synthetic pathways to tetrahydrocannabinol (THC): an overview

This review summarises various synthetic pathways leading to tetrahydrocannabinol and structurally related cannabinoids.

Graphical abstract: Synthetic pathways to tetrahydrocannabinol (THC): an overview
From the themed collection: Total synthesis in OBC
Review Article

Recent progress in the total synthesis of Strychnos alkaloids

The recent synthetic approaches toward Strychnos alkaloids are summarized, including novel synthetic methodologies and strategies.

Graphical abstract: Recent progress in the total synthesis of Strychnos alkaloids
From the themed collection: Total synthesis in OBC
Review Article

Recent progress in the total synthesis of marine brominated sesquiterpene aplydactone

In this review, we summarize five instructive total syntheses of marine brominated sesquiterpene aplydactone developed over the past five years.

Graphical abstract: Recent progress in the total synthesis of marine brominated sesquiterpene aplydactone
From the themed collection: Total synthesis in OBC
Review Article

Synthetic approaches towards avibactam and other diazabicyclooctane β-lactamase inhibitors

The synthetic strategies to obtain avibactam and other diazabicyclooctane β-lactamase inhibitors such as ETX2514 are presented.

Graphical abstract: Synthetic approaches towards avibactam and other diazabicyclooctane β-lactamase inhibitors
From the themed collection: Total synthesis in OBC
Review Article

Full solid-phase total synthesis of macrocyclic natural peptides using four-dimensionally orthogonal protective groups

This review focuses on four-dimensionally orthogonal protective group strategies for the full solid-phase synthesis of macrocyclic natural peptides.

Graphical abstract: Full solid-phase total synthesis of macrocyclic natural peptides using four-dimensionally orthogonal protective groups
From the themed collection: Total synthesis in OBC
Review Article

Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis

Versatility of glycals in the stereoselective synthesis of natural products.

Graphical abstract: Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis
From the themed collection: Chemical Biology in OBC
Review Article

Progress in total synthesis of subincanadine alkaloids and their congeners

Total synthesis of subincanadine alkaloids and their biogenetic congeners are described in a focused manner.

Graphical abstract: Progress in total synthesis of subincanadine alkaloids and their congeners
From the themed collection: Total synthesis in OBC
Review Article

Recent advances in the synthesis of azaphenalene alkaloids: first enantioselective approaches

This review provides an update of the synthetic progress towards azaphenalene alkaloids, including the pioneering enantioselective approaches.

Graphical abstract: Recent advances in the synthesis of azaphenalene alkaloids: first enantioselective approaches
From the themed collection: Total synthesis in OBC
Review Article

Natural products as modulators of the cyclic-AMP pathway: evaluation and synthesis of lead compounds

Natural product modulators of the cAMP pathway have been evaluated and their total synthesis campaign is described in detail.

Graphical abstract: Natural products as modulators of the cyclic-AMP pathway: evaluation and synthesis of lead compounds
From the themed collection: Total synthesis in OBC
Review Article

Review of synthetic approaches toward maoecrystal V

Synthetic approaches toward the complex natural product diterpenoid maoecrystal V are reviewed, including successful total syntheses, published synthetic efforts, and efforts compiled from dissertations.

Graphical abstract: Review of synthetic approaches toward maoecrystal V
From the themed collection: Total synthesis in OBC
Review Article

Total synthesis of complex alkaloids by nucleophilic addition to amides

This mini review focuses on the recent progress of total synthesis of complex alkaloids based on the nucleophilic additions to N-alkoxyamides, tertiary amides and secondary amides.

Graphical abstract: Total synthesis of complex alkaloids by nucleophilic addition to amides
From the themed collection: Total synthesis in OBC
Communication

Total syntheses of (+)-adunctins C and D: assignment of their absolute configurations

The first asymmetric synthesis of adunctins C and D was achieved, thus enabling the assignment of the absolute configurations of these two natural products.

Graphical abstract: Total syntheses of (+)-adunctins C and D: assignment of their absolute configurations
From the themed collection: Total synthesis in OBC
Communication

Toward the synthesis of the hypoxia selective anticancer agent BE-43547 A2

The stereoselective synthesis of the 19-epi-BE-43547 A2 chiral framework is achieved from D-glucose by employing an unusual (Z)-selective Julia–Kocienski olefination and hydroboration as key steps.

Graphical abstract: Toward the synthesis of the hypoxia selective anticancer agent BE-43547 A2
From the themed collection: Total synthesis in OBC
Open Access Communication

Synthesis of tetracyclic spiroindolines by an interrupted Bischler–Napieralski reaction: total synthesis of akuammicine

The interrupted Bischler–Napieralski reaction of β,γ-unsaturated tryptamides affords tetracyclic spiro pyrroloindolines, which can be used in the total synthesis of the Strychnos alkaloid, akuammicine.

Graphical abstract: Synthesis of tetracyclic spiroindolines by an interrupted Bischler–Napieralski reaction: total synthesis of akuammicine
From the themed collection: Total synthesis in OBC
Communication

A multifunctional divergent scaffold to access the formal syntheses of various sesquiterpenoids

A new divergent scaffold for the synthesis of various sesquiterpenoids in furan and α,β-unsaturated lactone oxidation states was developed through a novel, concise and scalable route.

Graphical abstract: A multifunctional divergent scaffold to access the formal syntheses of various sesquiterpenoids
From the themed collection: Total synthesis in OBC
Communication

A three-step enantioselective synthesis of (+)- and (−)-α-thujone

An asymmetric synthesis of α-thujone was achieved with a gold-catalyzed cycloisomerization as the key step. The route provides access either enantiomer of the natural product without the use of protecting groups or redox manipulations.

Graphical abstract: A three-step enantioselective synthesis of (+)- and (−)-α-thujone
From the themed collection: Total synthesis in OBC
Communication

Ambruticins: tetrahydropyran ring formation and total synthesis

The total synthesis of ambruticin J and epoxidation/cyclisation studies on model unsaturated hydroxy esters are described.

Graphical abstract: Ambruticins: tetrahydropyran ring formation and total synthesis
From the themed collection: Total synthesis in OBC
Communication

Total syntheses of melodienones by redox isomerization of propargylic alcohols

A remarkable base-promoted methodology for the rapid construction of the (E)- and (Z)-γ-oxo-α,β-alkenoic ester skeletons from readily accessible vinyl propargylic alcohols through modified redox isomerization was uncovered.

Graphical abstract: Total syntheses of melodienones by redox isomerization of propargylic alcohols
From the themed collection: Total synthesis in OBC
Communication

Synthesis of an isomer of lycoplanine A via cascade cyclization to construct the spiro-N,O-acetal moiety

A 6/10/5/5 tetracyclic isomer of lycoplanine A is synthesized using D–A reaction and cascade cyclization to respectively establish the [9.2.2] pentadecane skeleton and spirocenter, providing sufficient experience to synthesize lycoplanine A.

Graphical abstract: Synthesis of an isomer of lycoplanine A via cascade cyclization to construct the spiro-N,O-acetal moiety
From the themed collection: Total synthesis in OBC
Communication

Enantioselective total synthesis of (+)-ieodomycin A, (+)-ieodomycin B, and their three stereoisomers

Enantioselective routes for the total synthesis of ieodomycins A & B, and three stereochemical analogues of ieodomycin B via a late-stage elaboration of the side chain.

Graphical abstract: Enantioselective total synthesis of (+)-ieodomycin A, (+)-ieodomycin B, and their three stereoisomers
From the themed collection: Total synthesis in OBC
Communication

Total synthesis of thioamycolamide A via a biomimetic route

A concise total synthesis of thioamycolamide A was accomplished as a key step of thio-Michael addition via a biomimetic route.

Graphical abstract: Total synthesis of thioamycolamide A via a biomimetic route
From the themed collection: Total synthesis in OBC
Communication

Total synthesis of tubulysin U and N14-desacetoxytubulysin H

A concise and efficient procedure for the total synthesis of tubulysin U and N14-desacetoxytubulysin H has been developed with high stereoselectivity on a gram scale.

Graphical abstract: Total synthesis of tubulysin U and N14-desacetoxytubulysin H
From the themed collection: Total synthesis in OBC
Communication

Stereoselective synthesis of an eleganine A core

The core structure of eleganine A – a cytotoxic indole monoterpene alkaloid – was accessed for the first time.

Graphical abstract: Stereoselective synthesis of an eleganine A core
From the themed collection: Total synthesis in OBC
Communication

Synthesis of B-ring-fluorinated (−)-epicatechin gallate derivatives

Electronically modified, fluorinated catechins and epicatechins are enantioselectively synthesized in a short, convergent sequence via kinetic resolution.

Graphical abstract: Synthesis of B-ring-fluorinated (−)-epicatechin gallate derivatives
From the themed collection: Total synthesis in OBC
Communication

Divergent syntheses of okaramines C, J, L, and S–U

The first total synthesis of okaramines L and S–U, and the concise synthesis of okaramines C and J have been accomplished using a common intermediate bromohexahydropyrroloindole in 5–8 steps with an overall yield of 6.7%–23.0%.

Graphical abstract: Divergent syntheses of okaramines C, J, L, and S–U
From the themed collection: Total synthesis in OBC
Communication

Total synthesis of tricolorin A via interrupted Pummerer reaction-mediated glycosylation and one-pot relay glycosylation

The total synthesis of tricolorin A was achieved with high efficiency based on interrupted Pummerer reaction-mediated (IPRm) glycosylation and one-pot relay glycosylation.

Graphical abstract: Total synthesis of tricolorin A via interrupted Pummerer reaction-mediated glycosylation and one-pot relay glycosylation
From the themed collection: Total synthesis in OBC
Communication

Total synthesis of isatindigotindoline C

Total synthesis of isatindigotindoline C is achieved in two steps using a biomimetic 1,3-dipolar cycloaddition reaction as the key step.

Graphical abstract: Total synthesis of isatindigotindoline C
From the themed collection: Total synthesis in OBC
Communication

Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: insight into the origin of the high regioselectivity of annulation

Reported herein is a viable synthesis route to procyanidins A1 and A2, doubly linked flavan dimers. The use of nascent nucleophilic partner, catechin or epicatechin, enabled facile regioselective annulation with an ethylenedioxy-bridged flavan unit.

Graphical abstract: Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: insight into the origin of the high regioselectivity of annulation
From the themed collection: Total synthesis in OBC
Communication

Facile access to evodiakine enabled by aerobic copper-catalyzed oxidative rearrangement

Oxidative rearrangement for the first rapid construction of evodiakine was developed.

Graphical abstract: Facile access to evodiakine enabled by aerobic copper-catalyzed oxidative rearrangement
From the themed collection: Total synthesis in OBC
Communication

Total syntheses of seminolipid and its analogues by using 2,6-bis(trifluoromethyl)phenylboronic acid as protective reagent

Total synthesis of seminolipid was accomplished via regioselective protection using 2,6-bis(trifluoromethyl)phenylboronic acid followed by regioselective trichloroethyl-protected sulfation as key steps.

Graphical abstract: Total syntheses of seminolipid and its analogues by using 2,6-bis(trifluoromethyl)phenylboronic acid as protective reagent
From the themed collection: Total synthesis in OBC
Communication

Total synthesis of (+)-ar-macrocarpene

First total synthesis of a naturally occurring sesquiterpenoid, (+)-ar-macrocarpene, has been achieved via a key [3,3]-sigmatropic rearrangement effecting reductive transposition through allylic diazene rearrangement (ADR).

Graphical abstract: Total synthesis of (+)-ar-macrocarpene
From the themed collection: Synthetic methodology in OBC
Open Access Communication

A biomimetic approach towards phorone sesterterpenoids

We report efforts towards a unified total synthesis of Korean sponge derived sesterterpenoids phorones A and B, using a biomimetic strategy. This work has established a new synthetic approach to the parent ansellane sesterterpenoid skeleton with unanticipated diversion along a biogenetically related pathway.

Graphical abstract: A biomimetic approach towards phorone sesterterpenoids
From the themed collection: Total synthesis in OBC
Communication

Total synthesis of (±)-epi-stemodan-13α,17-diol

Stemodan-13α,17-diol is a natural stemodane-type diterpenoid isolated from Stemodia chilensis.

Graphical abstract: Total synthesis of (±)-epi-stemodan-13α,17-diol
From the themed collection: Total synthesis in OBC
Communication

A new route to tricyclane sesquiterpenoids: total synthesis of α-ekasantalic acid

Chemical manipulation of the cycloadduct of citraconic anhydride and cyclopentadiene enables a new synthetic route to tricyclane sesquiterpenoids.

Graphical abstract: A new route to tricyclane sesquiterpenoids: total synthesis of α-ekasantalic acid
From the themed collection: Total synthesis in OBC
Communication

Total synthesis of (±)-antroquinonol

We report the total synthesis of (±)-antroquinonol based on a concise and efficient route.

Graphical abstract: Total synthesis of (±)-antroquinonol
From the themed collection: Total synthesis in OBC
Communication

Palladium-catalyzed intramolecular carboborylation of 1,3-diene and synthesis of ABCD ring of communesins

A palladium-catalyzed intramolecular carboborylation of 1,3-diene has been developed for the synthesis of iminoindolines with a quaternary carbon centre.

Graphical abstract: Palladium-catalyzed intramolecular carboborylation of 1,3-diene and synthesis of ABCD ring of communesins
From the themed collection: Total synthesis in OBC
Communication

Synthesis of the core structure of phalarine

Two new palladium-catalyzed reactions enabled the synthesis of the core structure of phalarine.

Graphical abstract: Synthesis of the core structure of phalarine
From the themed collection: Total synthesis in OBC
Open Access Communication

Total synthesis of incargranine A

Synthetic studies into the origins of the alkaloid incargranine A have resulted in the development of a four-step (longest linear sequence) total synthesis.

Graphical abstract: Total synthesis of incargranine A
From the themed collection: Total synthesis in OBC
Communication

Synthesis and biological evaluation of fluorinated analogues of ripostatin A

A last stage click-chemistry approach to synthesize the heterocycle-containing derivatives of fluorinated ripostatin A was developed.

Graphical abstract: Synthesis and biological evaluation of fluorinated analogues of ripostatin A
From the themed collection: Total synthesis in OBC
Communication

Enantioselective synthesis and absolute configuration determination of hydroxywilfordic acid in sesquiterpene pyridine alkaloids

An enantioselective synthetic route to hydroxywilfordic acid, a key subunit of sesquiterpene pyridine alkaloids such as wilfortrine, was developed.

Graphical abstract: Enantioselective synthesis and absolute configuration determination of hydroxywilfordic acid in sesquiterpene pyridine alkaloids
From the themed collection: Total synthesis in OBC
Communication

Total synthesis of the potent anti-inflammatory natural product solomonamide A along with structural revision and biological activity evaluation

Herein, we report the total synthesis of solomonamide A along with its structural revision for the first time.

Graphical abstract: Total synthesis of the potent anti-inflammatory natural product solomonamide A along with structural revision and biological activity evaluation
From the themed collection: Total synthesis in OBC
Communication

Syntheses of the plant auxin conjugate 2-O-(indole-3-acetyl)-myo-inositol IAInos

The two first chemical syntheses of IAInos (2-O-(indole-3-acetyl)-myo-inositol), an important plant hormone, are described.

Graphical abstract: Syntheses of the plant auxin conjugate 2-O-(indole-3-acetyl)-myo-inositol IAInos
From the themed collection: Total synthesis in OBC
Communication

Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol

We describe semi-syntheses of the 11-hydroxyrotenoids sumatrol (1) and villosinol (2), starting from rotenone (5), using an oxime-directed C11–H functionalisation approach.

Graphical abstract: Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol
From the themed collection: Total synthesis in OBC
Communication

Biomimetic total syntheses of chromane meroterpenoids, guadials B and C, guapsidial A and psiguajadial D

The first biomimetic total syntheses of chromane meroterpenoids, guadials B and C, guapsidial A and psiguajadial D have been completed.

Graphical abstract: Biomimetic total syntheses of chromane meroterpenoids, guadials B and C, guapsidial A and psiguajadial D
From the themed collection: Total synthesis in OBC
Communication

Synthesis of two new gem-fluoronitro containing tetranitroadamantanes and property comparison with their nitro and gem-dinitro analogues

Two new fluorinated tetranitroadamantanes were synthesized and their physical properties were compared with their analogues on the basis of experimental and calculated results.

Graphical abstract: Synthesis of two new gem-fluoronitro containing tetranitroadamantanes and property comparison with their nitro and gem-dinitro analogues
From the themed collection: Total synthesis in OBC
Communication

Synthesis of the [7-5-5] tricyclic core of Daphniphyllum alkaloids

The [7-5-5] tricyclic core of the Daphniphyllum alkaloids was constructed, featuring a Claisen-Ireland rearrangement to install the two contiguous stereogenic centers, E1cB elimination to form the tetrasubstituted C–C double bond, and a 2,3-Wittig rearrangement to construct the quaternary carbon.

Graphical abstract: Synthesis of the [7-5-5] tricyclic core of Daphniphyllum alkaloids
From the themed collection: Total synthesis in OBC
Communication

Stereoselective preparation of key intermediates for the synthesis of iso-, neuro- and phyto-prostane family members: inaugural asymmetric synthesis of 17-E2c-dihomo- and 17-F2c-dihomo-isoprostanes

A practical synthesis of enantiopure key intermediates for the preparation of prostanoids has been described.

Graphical abstract: Stereoselective preparation of key intermediates for the synthesis of iso-, neuro- and phyto-prostane family members: inaugural asymmetric synthesis of 17-E2c-dihomo- and 17-F2c-dihomo-isoprostanes
From the themed collection: Total synthesis in OBC
Accepted Manuscript - Paper

Synthesis of illudalic acid and analogous phosphatase inhibitors

From the themed collection: Total synthesis in OBC
Paper

Diastereoselective synthesis of (±)-trichodiene and (±)-trichodiene-D3 as analytical standards for the on-site quantification of trichothecenes

A new RCM-based, divergent synthetic strategy towards native and deuterium labeled (±)-trichodiene is presented.

Graphical abstract: Diastereoselective synthesis of (±)-trichodiene and (±)-trichodiene-D3 as analytical standards for the on-site quantification of trichothecenes
From the themed collection: Total synthesis in OBC
Paper

A modular strategy for the synthesis of marine originated meroterpenoid-type natural products

Chemoselective formal synthesis of (−)-pelorol and 9-epi-pelorol was achieved by controlling the reaction sequence of hydrogenation and cyclization. Synthesis of (+)-yahazunone and (+)-yahazunol was also accomplished using palladium-catalyzed tandem carbene migratory insertion.

Graphical abstract: A modular strategy for the synthesis of marine originated meroterpenoid-type natural products
From the themed collection: Total synthesis in OBC
Paper

Stereocomplementary synthesis of casuarine and its 6-epi-, 7-epi-, and 6,7-diepi-stereoisomers

A stereocomplementary strategy allows the efficient synthesis of casuarine, 6-epi-casuarine, 7-epi-casuarine, and 6,7-diepi-casuarine from a cyclic nitrone and a nitrone-derived aldehyde. Their glycosidase inhibition profiles were compared.

Graphical abstract: Stereocomplementary synthesis of casuarine and its 6-epi-, 7-epi-, and 6,7-diepi-stereoisomers
From the themed collection: Total synthesis in OBC
Paper

Oxazaborolidine-catalyzed reductive parallel kinetic resolution of ketones from β-nitro-azabicycles for the synthesis of chiral hypoestestatins 1, 2

Total synthesis of 13a-methyl tylophora alkaloids and related compounds from β-nitro-azabicycles were reported. Parallel kinetic resolution provided both enantiomers of hypoestestatins 1 and 2.

Graphical abstract: Oxazaborolidine-catalyzed reductive parallel kinetic resolution of ketones from β-nitro-azabicycles for the synthesis of chiral hypoestestatins 1, 2
From the themed collection: Total synthesis in OBC
Paper

Double asymmetric intramolecular aza-Michael reaction: a convenient strategy for the synthesis of quinolizidine alkaloids

A new strategy for the asymmetric synthesis of the quinolizidine skeleton via double intramolecular aza-Michael reaction of sulfinyl amines bearing a bis-enone moiety is described. This is the shortest route towards quinolizidines reported to date.

Graphical abstract: Double asymmetric intramolecular aza-Michael reaction: a convenient strategy for the synthesis of quinolizidine alkaloids
From the themed collection: Total synthesis in OBC
Paper

Total syntheses and antiproliferative activities of prenostodione and its analogues

The synthesis of prenostodione and analogues was accomplished, and their antiproliferative activities were determined and compared with those of commercial drugs etoposide and cisplatin.

Graphical abstract: Total syntheses and antiproliferative activities of prenostodione and its analogues
From the themed collection: Total synthesis in OBC
Paper

Enantioselective construction of substituted pyridine and a seven-membered carbocyclic skeleton: biomimetic synthesis of (−)-rupestine D, (−)-guaipyridine, (−)-epiguaipyridine, and (−)-cananodine and their stereoisomers

Guaipyridine alkaloids (−)-rupestine D, (−)-guaipyridine, (−)-epiguaipyridine, and (−)-cananodine together with two stereoisomers 8-epi-rupestine D and 5-epi-cananodine were synthesized enantioselectively from readily available citronellol.

Graphical abstract: Enantioselective construction of substituted pyridine and a seven-membered carbocyclic skeleton: biomimetic synthesis of (−)-rupestine D, (−)-guaipyridine, (−)-epiguaipyridine, and (−)-cananodine and their stereoisomers
From the themed collection: Total synthesis in OBC
Paper

Asymmetric synthesis of (−)-dehydro-exo-brevicomin with a photoisomerisation–intramolecular acetalisation sequence

We have accomplished the asymmetric synthesis of (−)-dehydro-exo-brevicomin in a practical and scalable manner via a possible biosynthetic precursor obtained by photoisomerisation.

Graphical abstract: Asymmetric synthesis of (−)-dehydro-exo-brevicomin with a photoisomerisation–intramolecular acetalisation sequence
From the themed collection: Total synthesis in OBC
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The latest articles published in Organic and Biomolecular Chemistry related to total synthesis.

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