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

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.

Laurence Grimaud, Delphine Rotulo, Rafael Ros-Perez, Ludivine Guitry-Azam, Joëlle Prunet. Synthesis of protected syn 1,3-diols by intramolecular conjugate addition to vinyl sulfones. Tetrahedron Letters, 2002, 43 (42), pp.7477-7479. ⟨10.1016/s0040-4039(02)01796-3⟩. ⟨hal-00954862⟩