Themed collection Total synthesis in OBC

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.

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.

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

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

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.

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

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.

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

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.

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.

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

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.

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

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

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

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

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

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

Versatility of glycals in the stereoselective synthesis of natural products.

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

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

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

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

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.

A facile Stevens rearrangement of the Weinreb amide and the subsequent key steps mediated by the carbonyl of the Weinreb amide led to the construction of azaspirocyclic skeletons of some typical alkaloids.

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

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.

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.

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.

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.

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

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.

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.

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.

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

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.

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

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

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%.

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

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

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.

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

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.

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).

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.

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

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

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

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

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

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

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

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

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

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

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.

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

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

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.

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

The first synthesis of micrococcin P2 has been achieved by late-stage Suzuki coupling of a macrocyclic boronic acid with a 2-bromothiazole.

Efforts to validate the proposed biosynthesis of pegaharmaline A led to the formation of several new heteroaromatic scaffolds.

A unified approach leading to benzo[d][1,3]dioxole-type benzylisoquinoline alkaloids of aporphines, coptisines, and dibenzopyrrocolines.

Studies directed towards the stereoselective synthesis of the diarylheptanoid-derived natural products hedycoropyrans leading to the total synthesis of (−)-hedycoropyran B (ent-rhoiptelol B) are presented.

A convergent 5-step synthesis (LLS) of illudalic acid allows for concise preparation of analogues for pharmacological evaluation.

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

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.

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.