Asymmetric Synthesis of the Chlorocyclopropane-Containing Callipeltoside A Side Chain

The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-d-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allyli...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2001-02, Vol.3 (4), p.503-505
Main Authors: Evans, David A, Burch, Jason D
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Cyclopropanes - chemical synthesis
Macrolides
Mannitol - analogs & derivatives
Mannitol - chemistry
Molecular Structure
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-d-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0155182