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A non-iterative, flexible, and highly stereoselective synthesis of polydeoxypropionates--synthesis of (+)-vittatalactone.

Authors
  • Weise, Christian F
  • Pischl, Matthias
  • Pfaltz, Andreas
  • Schneider, Christoph
Type
Published Article
Journal
Chemical Communications
Publisher
The Royal Society of Chemistry
Publication Date
Mar 21, 2011
Volume
47
Issue
11
Pages
3248–3250
Identifiers
DOI: 10.1039/c0cc05215a
PMID: 21279191
Source
Medline
License
Unknown

Abstract

A short sequence comprising an oxy-Cope rearrangement, iridium-catalyzed hydrogenation, and enolate methylation provides trideoxypropionates with excellent diastereocontrol. A straightforward synthesis of the cucumber beetle pheromone (+)-vittatalactone illustrates this new strategy.

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