Synthesis of protected syn 1,3-diols by intramolecular conjugate addition to vinyl sulfones

Abstract : A short route to sulfones 9a-c is described. These synthons encompassing a syn 1,3-diol motif are model compounds for the C16-C24 fragment of Dolabelides. The benzylidene protecting group can be reduced regioselectively to furnish ß-hydroxysulfones 10a-b. First attempts of Julia coupling of the dianions derived from these substrates with aldehydes and ketones are also reported. © 2002 Elsevier Science Ltd. All rights reserved.