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Themed collection Total synthesis in OBC

22 items
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
Accepted Manuscript - Communication

Biomimetic Total Syntheses of Chromane Meroterpenoids, Guadials B-C, Guapsidial A and Psiguajadial D

From the themed collection: Total synthesis in OBC
Accepted Manuscript - Communication

Synthesis of two new gem-fluoronitro contained 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

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
22 items

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

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