Concise Total Synthesis of (±)-Crinine

Abstract The concise total synthesis of (±)-crinine was accomplished in 24% overall yield and eleven steps starting from an easily available allylic alcohol. The key step of the current synthesis involved the NBS-promoted semipinacol rearrangement reaction of allylic alcohols. The hydroindole skelet...

Full description

Saved in:
Bibliographic Details
Published in:Synlett 2009-11, Vol.2009 (18), p.3040-3042
Main Authors: Liu, Jian-Dong, Wang, Shao-Hua, Zhang, Fu-Min, Tu, Yong-Qiang, Zhang, Yong-Qiang
Format: Article
Language:English
Subjects:
letter
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Abstract The concise total synthesis of (±)-crinine was accomplished in 24% overall yield and eleven steps starting from an easily available allylic alcohol. The key step of the current synthesis involved the NBS-promoted semipinacol rearrangement reaction of allylic alcohols. The hydroindole skeleton with the sterically congested quaternary carbon center was established concisely by utilizing this semipinacol rearrangement followed by a combination of intramolecular aldol and aza-Michael reactions.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0029-1218296