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Themed collection Total synthesis in OBC

39 items
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
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

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: New Talent
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: New Talent
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
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
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
Communication

Concise total synthesis of (+)-asperazine A and (+)-pestalazine B

The highly convergent total synthesis of dimeric diketopiperazine alkaloids (+)-asperazine A and (+)-pestalazine B is described.

Graphical abstract: Concise total synthesis of (+)-asperazine A and (+)-pestalazine B
From the themed collection: Synthetic methodology in OBC
Paper

First enantioselective total synthesis of altersolanol A

The first enantioselective total synthesis of altersolanol A was accomplished by Diels–Alder cycloaddition promoted by (R)-3,3′-BINOL/boron Lewis acid.

Graphical abstract: First enantioselective total synthesis of altersolanol A
From the themed collection: Total synthesis in OBC
Paper

Synthesis of macrocyclic precursors of the vioprolides

Convergent syntheses have been developed of macrocycles that may be useful for the synthesis of vioprolide D. Preliminary studies have also been carried out into the introduction of the thiazoline and (E)-dehydrobutyrine components.

Graphical abstract: Synthesis of macrocyclic precursors of the vioprolides
From the themed collection: Total synthesis in OBC
Paper

Toward the total synthesis of patellazole B: synthesis of an advanced C1–C25 fragment corresponding to the macrocyclic skeleton

A modular and highly convergent approach enables the assembly of an advanced intermediate towards the total synthesis of patellazole B – a promising anticancer agent.

Graphical abstract: Toward the total synthesis of patellazole B: synthesis of an advanced C1–C25 fragment corresponding to the macrocyclic skeleton
Paper

Studies toward the synthesis of strevertenes A and G: stereoselective construction of C1–C19 segments of the molecules

Efficient route for the stereoselective synthesis of common C1–C19 segment of strevertenes A and G has been developed.

Graphical abstract: Studies toward the synthesis of strevertenes A and G: stereoselective construction of C1–C19 segments of the molecules
Paper

Functionalization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A–E, G, Q and their analogues

Diastereoselective aldol condensation of diazotetronic acid and a subsequent arene C–H insertion provides an efficient route to the aspulvinone motif.

Graphical abstract: Functionalization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A–E, G, Q and their analogues
From the themed collection: Total synthesis in OBC
Paper

Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction

Enantioselective syntheses of decytospolides are described using an Achmatowicz rearrangement, transfer hydrogenation and Friedel–Crafts acylation as the key steps.

Graphical abstract: Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction
From the themed collection: Total synthesis in OBC
Paper

Enantioselective total synthesis and biological evaluation of (−)-solanacol

An enantioselective synthesis of the phenyl ring-containing strioglactone, (−)-solanocol, is described.

Graphical abstract: Enantioselective total synthesis and biological evaluation of (−)-solanacol
From the themed collection: Total synthesis in OBC
Paper

Total synthesis of the proposed structure of talarolide A

The proposed structure of talarolide A, a cycloheptapeptide featuring a hydroxamate moiety within the peptide backbone, was successfully synthesized.

Graphical abstract: Total synthesis of the proposed structure of talarolide A
From the themed collection: Synthetic methodology in OBC
Paper

Asymmetric total synthesis of naturally occurring spirocyclic tetranorsesquiterpenoid lanceolactone A

Asymmetric total synthesis of naturally occurring γ-butenolide containing [4.4]spiro-tetrahydrofuran lanceolactone A has been reported in this present work. Bimetallic (“Pd–Cu”) cascade cyclization was the crucial reaction employed for the construction of the γ-butenolide framework of the natural product.

Graphical abstract: Asymmetric total synthesis of naturally occurring spirocyclic tetranorsesquiterpenoid lanceolactone A
From the themed collection: Total synthesis in OBC
Paper

Total synthesis and structural revision of an isopanepoxydone analog isolated from Lentinus strigellus

Asymmetric total synthesis of compound 1, as a proposed molecular structure of a natural product, in 11 steps is described. The inconsistency of the characterization data prompted us to propose a different structure as compound 2 and accordingly accomplish total synthesis in 9 steps and confirm the structural revision of this natural product.

Graphical abstract: Total synthesis and structural revision of an isopanepoxydone analog isolated from Lentinus strigellus
From the themed collection: Total synthesis in OBC
Paper

Total synthesis and structural revision of (±)-nidemone

Total synthesis and structural revision of (±)-nidemone have been accomplished from 6-bromo-2-hydroxybenzaldehyde (5) in either six or eight synthetic steps.

Graphical abstract: Total synthesis and structural revision of (±)-nidemone
From the themed collection: Total synthesis in OBC
Paper

Total synthesis of 1α,25-dihydroxyvitamin D3 analogs modified at the side chain and D-ring

A general approach to generate the natural or unnatural steroid configuration at C20 and unsaturation at the D-ring is exemplified with the total synthesis of 1α,25-dihydroxyvitamin D3 analogs 3 and 4.

Graphical abstract: Total synthesis of 1α,25-dihydroxyvitamin D3 analogs modified at the side chain and D-ring
From the themed collection: Total synthesis in OBC
Paper

A convergent strategy towards febrifugine and related compounds

We report a modular five step synthetic route to the febrifugines that employs 2-(chloromethyl)allyl-trimethylsilane as a conjunctive reagent for the coupling of the piperidine and quinazolinone groups.

Graphical abstract: A convergent strategy towards febrifugine and related compounds
From the themed collection: Total synthesis in OBC
Paper

Synthetic studies toward the marine metabolite prorocentin-4: synthesis of the C1–C23 fragment

A synthetic study of the construction of the C1–C23 fragment of prorocentin-4, a novel linear polyketide, is described.

Graphical abstract: Synthetic studies toward the marine metabolite prorocentin-4: synthesis of the C1–C23 fragment
From the themed collection: Total synthesis in OBC
Paper

The first total synthesis of gobichelin B: a mixed-ligand siderophore of Streptomyces sp. NRRL F-4415

The first total synthesis of a structurally diverse mixed ligand siderophore, gobichelin B and an epi-gobichelin B is reported.

Graphical abstract: The first total synthesis of gobichelin B: a mixed-ligand siderophore of Streptomyces sp. NRRL F-4415
From the themed collection: Total synthesis in OBC
Paper

A novel approach to sesquiterpenoid benzoxazole synthesis from marine sponges: nakijinols A, B and E–G

Nakijinols A, B, E, F and G were efficiently synthesized via the ring closure of the N-(2-hydroxyphenyl)-formamide or -acetamide moiety.

Graphical abstract: A novel approach to sesquiterpenoid benzoxazole synthesis from marine sponges: nakijinols A, B and E–G
From the themed collection: Total synthesis in OBC
Paper

Total synthesis of the natural HDAC inhibitor Cyl-1

A chelate enolate Claisen rearrangement was used as a key step in the first total synthesis of Cyl-1, a cyclic tetrapeptide from Cylindrocladium scoparium.

Graphical abstract: Total synthesis of the natural HDAC inhibitor Cyl-1
From the themed collection: Total synthesis in OBC
Paper

Formal synthesis of cis-solamin: acid-catalyzed one-step construction of 2,5-disubstituted tetrahydrofuran

A concise and stereoselective synthesis of a 2,5-disubstituted tetrahydrofuran was developed and applied to the formal synthesis of cis-solamin.

Graphical abstract: Formal synthesis of cis-solamin: acid-catalyzed one-step construction of 2,5-disubstituted tetrahydrofuran
From the themed collection: Total synthesis in OBC
Open Access Paper

Synthesis and structural elucidation of a dehydrochloromethyltestosterone metabolite

The identity of a human long-term metabolite of the doping agent Oral Turinabol (DHCMT) is secured by the synthesis of all probable stereoisomers.

Graphical abstract: Synthesis and structural elucidation of a dehydrochloromethyltestosterone metabolite
From the themed collection: Total synthesis in OBC
Paper

Toward aplyronine payloads for antibody–drug conjugates: total synthesis of aplyronines A and D

We report an expedient total synthesis of aplyronines A and D, together with a linker-modified analogue for bioconjugation studies.

Graphical abstract: Toward aplyronine payloads for antibody–drug conjugates: total synthesis of aplyronines A and D
From the themed collection: Total synthesis in OBC
Open Access Paper

Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

Three steps suffice to complete a bioinspired total synthesis of tetrahydrofuran lignans using tandem addition/isomerization/dimerization and cycloetherification reactions.

Graphical abstract: Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps
From the themed collection: Total synthesis in OBC
Paper

Total synthesis of selaginpulvilins A and C

An efficient strategy for the formal total synthesis of selaginpulvilins A and C has been reported. This approach involves 6 and 7 linear synthetic operations and is associated with 10% and 7% overall yields respectively for selaginpulvilins A and C.

Graphical abstract: Total synthesis of selaginpulvilins A and C
From the themed collection: Total synthesis in OBC
Paper

Synthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromatics

Alternative sources of potential feedstock chemicals are of increasing importance as the availability of oil decreases.

Graphical abstract: Synthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromatics
From the themed collection: Total synthesis in OBC
Paper

Design and synthesis of a hybrid framework of indanone and chromane: total synthesis of a homoisoflavanoid, brazilane

A chemical backbone of tetracyclic homoisoflavanoid natural products such as brazilin inspired us to design a new chemical scaffold, 6a,11b-dihydroindeno[2,1-c]chromen-7(6H)-one, which is a hybrid structure of indanone and chromane.

Graphical abstract: Design and synthesis of a hybrid framework of indanone and chromane: total synthesis of a homoisoflavanoid, brazilane
From the themed collection: Synthetic methodology in OBC
Paper

The direct and highly diastereoselective synthesis of 3,4-epoxy-2-piperidones. Application to the total synthesis and absolute configurational assignment of 3α,4α-epoxy-5β-pipermethystine

The substrate-controlled asymmetric total synthesis and absolute configurational assignment of biologically active 3α,4α-epoxy-5β-pipermethystine is reported.

Graphical abstract: The direct and highly diastereoselective synthesis of 3,4-epoxy-2-piperidones. Application to the total synthesis and absolute configurational assignment of 3α,4α-epoxy-5β-pipermethystine
From the themed collection: Total synthesis in OBC
39 items

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The latest articles published in Organic and Biomolecular Chemistry related to total synthesis.

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