Enantioselective Total Synthesis of Fortalpinoid Q via a TEMPO⁺BF₄^–-Mediated Dehydrative Nazarov Cyclization

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

The family of Cephalotaxus diterpenoids represents a captivating class natural products that are significant interest from both structural and biological perspectives within our community. Here we wish to report 15-step, enantioselective total synthesis the diterpenoid fortalpinoid Q. Our approach highlights (1) Jacobsen's catalytic Claisen rearrangement enabled single-step formation two vicinal stereogenic centers, including an all-carbon quaternary center; (2) mild, oxoammonium salt (TEMPO+BF4-)-promoted dehydrative Nazarov cyclization swiftly forged crucial cyclopentadiene moiety via unfunctionalized tertiary divinyl carbinol (TDC) substrate; (3) facile aldol-lactonization cascade ultimately resolved last obstacle in synthesis.

Language: Английский

The Latest Progress in the Chemistry of Daphniphyllum Alkaloids

Molecules, Journal Year: 2024, Volume and Issue: 29(23), P. 5498 - 5498

Published: Nov. 21, 2024

alkaloids (DAs) are interesting molecules with rich molecular skeletons and diverse biological activities. Since their discovery, phytochemists have isolated, purified, identified more than 350 DAs. Synthetic chemists, attracted by the structure activity of DAs, accomplished many elegant synthetic jobs. Herein, we summarize work on isolation, structural identification, bioactivity testing, synthesis DAs from 2018 to 2023, aim providing a reference for future studies.

Language: Английский