In the presence of a Lewis or protic acid and at low temperature, 1,3-dioxy-1,3-dienes add to sulfur dioxide generating zwitterionic intermediates that can react with carbon nucleophiles such as allylsilanes. After a retro-ene elimination of SO2, valuable polyketide precursors are obtained.
Title
Synthesis of long-chain polyketide fragments by reaction of 1,3-dioxy-1,3-dienes with allylsilanes: Umpolung with sulfur dioxide
Published in
Organic Letters
Volume
6
Issue
6
Pages
1053-1056
Date
2004
ISSN
1523-7060
Note
Swiss Fed Inst Technol, Inst Mol & Biol Chem, EPFL, BCH, CH-1015 Lausanne, Switzerland.
Record creation date
2005-11-09