Sulfinyl Moiety as an Internal Nucleophile. 1. Efficient Stereoselective Synthesis of Fragment A of Cryptophycin 3

A novel, efficient, and stereoselective synthesis of fragment A of cryptophycin 3 is disclosed. The key step involves the regio- and stereoselective transformation of an unsaturated ester to a bromohydrin via anchimeric assistance by the sulfinyl group.

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Bibliographic Details
Published in:Journal of organic chemistry 2003-06, Vol.68 (12), p.5002-5005
Main Authors: Raghavan, Sadagopan, Tony, K. A
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Combinatorial Chemistry Techniques
Cyanobacteria - chemistry
Depsipeptides
Exact sciences and technology
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Organic chemistry
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Preparations and properties
Stereoisomerism
Sulfoxides - chemistry
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Description
Summary:A novel, efficient, and stereoselective synthesis of fragment A of cryptophycin 3 is disclosed. The key step involves the regio- and stereoselective transformation of an unsaturated ester to a bromohydrin via anchimeric assistance by the sulfinyl group.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo026802p