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Tandem conjugate addition-elimination for the diastereoselective synthesis of 4E-alkenyl syn-1,3-diols.

Rotulo-Sims D, Prunet J

Laboratoire de Synthèse Organique, UMR CNRS 7652, Ecole Polytechnique, DCSO, F-91128 Palaiseau, France.

We 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.

Published 4 October 2007 in Org Lett, 9(21): 4147-50.
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