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Divergent and gram-scale syntheses of (–)-veratramine and (–)-cyclopamine

Authors :
Wenlong Hou
Hao Lin
Yanru Wu
Chuang Li
Jiajun Chen
Xiao-Yu Liu
Yong Qin
Source :
Nature Communications, Vol 15, Iss 1, Pp 1-6 (2024)
Publication Year :
2024
Publisher :
Nature Portfolio, 2024.

Abstract

Abstract Veratramine and cyclopamine, two of the most representative members of the isosteroidal alkaloids, are valuable molecules in agricultural and medicinal chemistry. While plant extraction of these compounds suffers from uncertain supply, efficient chemical synthesis approaches are in high demand. Here, we present concise, divergent, and scalable syntheses of veratramine and cyclopamine with 11% and 6.2% overall yield, respectively, from inexpensive dehydro-epi-androsterone. Our synthesis readily provides gram quantities of both target natural products by utilizing a biomimetic rearrangement to form the C-nor-D-homo steroid core and a stereoselective reductive coupling/(bis-)cyclization sequence to establish the (E)/F-ring moiety.

Subjects

Subjects :
Science

Details

Language :
English
ISSN :
20411723
Volume :
15
Issue :
1
Database :
Directory of Open Access Journals
Journal :
Nature Communications
Publication Type :
Academic Journal
Accession number :
edsdoj.63aef70f6f6454c98145ee531f29de9
Document Type :
article
Full Text :
https://doi.org/10.1038/s41467-024-49748-2