Synthesis of long-chain polyketide fragments by reaction of 1,3-dioxy-1,3-dienes with allylsilanes: Umpolung with sulfur dioxide

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.


Published in:
Organic Letters, 6, 6, 1053-1056
Year:
2004
ISSN:
1523-7060
Keywords:
Note:
Swiss Fed Inst Technol, Inst Mol & Biol Chem, EPFL, BCH, CH-1015 Lausanne, Switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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