Total Syntheses of Hosieines A-C

Authors

Jiayang Zhang
Xu Yan
Qing-Bao Zhang
Fang Wang
Bin Yang
Yang Yang

Language

English

Publication Date

4-1-2024

Journal

Advanced Science

DOI

10.1002/advs.202308164

PMID

38326080

PMCID

PMC11005691

PubMedCentral® Posted Date

4-11-2024

PubMedCentral® Full Text Version

Post-print

Abstract

The collective total syntheses of (±)-hosieines A-C with a cage-like tetracyclic framework have been realized, which includes the first syntheses of hosieines B-C. The key strategy of the synthesis employs a one-pot domino reaction that involves Cu-catalyzed [3+2] cycloaddition, 1,6-enone formation, and 1,6-aza-Michael addition forming the 5/6/6-aza-tricyclic skeleton. Other salient synthetic tactics comprise a challenging double bond migration and a 1,4-aza-Michael addition reaction to afford the tetracyclic framework.

Keywords

[3+2] reaction, alkaloids, natural products, one pot, total synthesis

Published Open-Access

yes

Recommended Citation

Zhang, Jiayang; Yan, Xu; Zhang, Qing-Bao; et al., "Total Syntheses of Hosieines A-C" (2024). Children’s Nutrition Research Center Staff Publications. 295.
https://digitalcommons.library.tmc.edu/staff_pub/295