Total Syntheses of (−)-Deoxoapodine, (−)-Kopsifoline D, and (−)-Beninine

Total Syntheses of (−)-Deoxoapodine, (−)-Kopsifoline D, and (−)-Beninine

The total syntheses of Aspidosperma and Kopsia alkaloids (−)-deoxoapodine, (−)-kopsifoline D, and (−)-beninine are described through a domino deprotection-Michael addition-nucleophilic substitution protocol to assemble the core framework in efficient steps. Corey–Bakshi–Shibata reduction was employe...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry Vol. 85; no. 2; pp. 967 - 976
Main Authors: Zhou, Yi-Guo, Wong, Henry N. C, Peng, Xiao-Shui
Format: Journal Article
Language:English
Published: United States American Chemical Society 17-01-2020
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The total syntheses of Aspidosperma and Kopsia alkaloids (−)-deoxoapodine, (−)-kopsifoline D, and (−)-beninine are described through a domino deprotection-Michael addition-nucleophilic substitution protocol to assemble the core framework in efficient steps. Corey–Bakshi–Shibata reduction was employed to afford the enantioenriched intermediate for the total syntheses of the aforementioned alkaloids. The chirality was shown to completely transfer to the backbone using Johnson–Claisen rearrangement. The enantioselective total syntheses of (−)-kopsifoline D and (−)-beninine were accomplished for the first time. Our strategy opens up practical avenues for the total synthesis of structurally similar alkaloids.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02918