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A general, asymmetric, and noniterative synthesis of trideoxypropionates. Straightforward syntheses of the pheromones (+)-vittatalactone and (+)-norvittatalactone.

Authors
  • Weise, Christian F
  • Pischl, Matthias C
  • Pfaltz, Andreas
  • Schneider, Christoph
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Feb 03, 2012
Volume
77
Issue
3
Pages
1477–1488
Identifiers
DOI: 10.1021/jo202330b
PMID: 22188256
Source
Medline
License
Unknown

Abstract

A novel, highly stereocontrolled, and very flexible synthetic access to biologically relevant trideoxypropionate building blocks in optically pure form has been developed. On the basis of a three-step sequence comprising a thermal oxy-Cope rearrangement, an iridium-catalyzed hydrogenation, and an auxiliary-controlled enolate methylation, trideoxypropionates with easily adjustable relative configuration were synthesized in excellent yields. In addition, the functionalized end groups allow for chemoselective manipulations and further elongation of the chain. The underlying strategy constitutes the first noniterative process for the assembly of polydeoxypropionates and has further been applied in total syntheses of the pheromones (+)-vittatalactone and (+)-norvittatalactone, which had been isolated from the striped cucumber beetle Acalymma vittatum.

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