Tandem Conjugate Addition-Elimination for the Diastereoselective Synthesis of 4E-Alkenyl syn 1,3-Diols

  • Rotulo-Sims, Delphine
  • Prunet, Joëlle
Publication date
January 2007
Publisher
American Chemical Society (ACS)

Abstract

4 pagesInternational audienceWe have developed a tandem conjugate addition-elimination sequence for the diastereoselective synthesis of protected allylic syn 1,3-diols, starting from vinyl sulfones. The sulfonyl group was then reduced with sodium amalgam to furnish the E olefin as the major isomer. This method was applied to the synthesis of a trisubstituted alkene modeling the C21-C25 fragment of Dolabelide C

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