Cephalotane diterpenoids: structural diversity, biological activity, biosynthetic proposal, and chemical synthesis

Natural Product Reports, Journal Year: 2024, Volume and Issue: 41(7), P. 1152 - 1179

Published: Jan. 1, 2024

Covering: up to the end of 2023Cephalotane diterpenoids are a unique class natural products exclusive genus Cephalotaxus, featuring rigid 7,6,5,6-fused tetracyclic architecture. The study cephalotanes dates back 1970s, when harringtonolide (1), Cephalotaxus troponoid with peculiar norditerpenoid carbon skeleton, was first discovered. In recent years, prototype C20 proposed as cephalotane were disclosed, which triggered intense studies on this diterpenoid family. To date, cumulative total 105 great structural diversity and biological importance have been isolated. addition, significant advances made in field synthesis biosynthesis years. This review provides complete overview chemical structures, bioactivities, biosynthetic aspects, completed all isolated diterpenoids, will help guide future research compounds.

Language: Английский

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Highly modified cephalotane-type diterpenoids from Cephalotaxus fortunei var. alpina and C. sinensis

Phytochemistry, Journal Year: 2024, Volume and Issue: 221, P. 114038 - 114038

Published: Feb. 21, 2024

Language: Английский

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Photoinduced copper-catalyzed selective three-component 1,2-amino oxygenation of 1,3-dienes

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(69), P. 10388 - 10391

Published: Jan. 1, 2023

This study presents a highly effective method for the photoinduced copper-catalyzed 1,2-amino oxygenation of 1,3-dienes. synthetic strategy involves dual roles single copper catalyst, which can act as photosensitizer to generate nitrogen radicals and also react with allyl via electron transfer (SET) processes. The produces range quaternary carbon-centered carboxylic esters tertiary ethers high yields excellent regioselectivity under mild reaction conditions.

Language: Английский

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Reductive Oxy-Nazarov Cyclization toward Expedient Construction of a Cyclopenta[1,2-b]pyrrolo[1,2-a]azepine Ring System: Formal Total Syntheses of Stemonamine and Cephalotaxine

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 5164 - 5169

Published: March 27, 2024

Formal total syntheses of stemonamine and cephalotaxine bearing the core cyclopenta[1,2-b]pyrrolo[1,2-a]azepine ring skeleton were achieved. The general synthetic strategy in synthesis features reductive oxy-Nazarov cyclization as key step, leading to versatile construction N-substituted spiro quaternary stereogenic centers from readily available starting materials.

Language: Английский

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Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110870 - 110870

Published: Jan. 1, 2025

Language: Английский

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Chemical diversity of pyrrolobenzazepine derivatives with a nodal nitrogen atom

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134524 - 134524

Published: Feb. 1, 2025

Language: Английский

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Advances in the analysis and application of metabolites from tropical plants

Current Opinion in Plant Biology, Journal Year: 2025, Volume and Issue: 85, P. 102728 - 102728

Published: April 24, 2025

Language: Английский

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Natural product–inspired bioactive alkaloids via C–C/C–N coupling reactions: Synthetic developments, current scenario, and future perspectives

Studies in natural products chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 39

Published: Jan. 1, 2025

Language: Английский

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Recent total synthesis of natural products leveraging a strategy of enamide cyclization

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 999 - 1009

Published: May 22, 2025

Enamides are distinctive amphiphilic synthons that can be strategically incorporated into cyclization reactions. The iminium species generated from enamides via nucleophilic addition or substitution capable of engaging in further electrophilic additions isomerization processes. Exploiting the multiple reactivities facilitates development diverse modes provide entries to various N -heterocycles, some which serve as key structural motifs natural alkaloids. This review highlights recent advancements enamide-based reactions, including enamide–alkyne cycloisomerization, [3 + 2] annulation, and polycyclization, with a particular emphasis on their pivotal role strategy total synthesis products.

Language: Английский

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Catalytic Asymmetric Polycyclization of Tertiary Enamides with Silyl Enol Ethers: Total Synthesis of (−)-Cephalocyclidin A

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(49), P. 26550 - 26556

Published: Nov. 29, 2023

A catalytic enantioselective polycyclization of tertiary enamides with terminal silyl enol ethers has been developed by virtue Cu(OTf)2 catalysis a novel spiropyrroline-derived oxazole (SPDO) ligand. This tandem reaction offers an effective approach to assemble bicyclic and tricyclic N-heterocycles bearing both aza- oxa-quaternary stereogenic centers, which are primal subunits in range natural alkaloids. Strategic application this methodology late-stage radical cyclization as key steps have showcased the concise total synthesis (−)-cephalocyclidin A.

Language: Английский

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