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

Laurence Grimaud; Delphine Rotulo; Rafael Ros-Perez; Ludivine Guitry-Azam; Joëlle Prunet

doi:10.1016/s0040-4039(02)01796-3

Journal articles

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

Laurence Grimaud ¹ Delphine Rotulo ¹ Rafael Ros-Perez ¹ Ludivine Guitry-Azam ¹ Joëlle Prunet ¹

1 DCSO - Laboratoire de synthèse organique

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.

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

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

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