Highly Enantioselective Approach to Indolizidines:  Preparation of (+)-(1S,8aS)-1-Hydroxyindolizidine and (−)-Slaframine

A highly stereoselective approach to (−)-slaframine and its probable biosynthetic precursor (+)-(1S,8aS)-1-hydroxyindolizidine has been developed based on a diastereofacially selective cycloaddition of dichloroketene with a chiral dienol ether.

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Bibliographic Details
Published in:Journal of organic chemistry 2000-10, Vol.65 (21), p.6966-6972
Main Authors: Pourashraf, Mehrnaz, Delair, Philippe, Rasmussen, Martin O, Greene, Andrew E
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Indolizines - chemical synthesis
Mycotoxins - chemical synthesis
Stereoisomerism
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Summary:A highly stereoselective approach to (−)-slaframine and its probable biosynthetic precursor (+)-(1S,8aS)-1-hydroxyindolizidine has been developed based on a diastereofacially selective cycloaddition of dichloroketene with a chiral dienol ether.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0005621