Tetrahedron p. 7557 - 7566 (1994)
Update date:2022-08-04
Topics: Cyclization Protecting groups Conjugate addition Starting Material Functional group manipulation Final steps Stereochemistry Control Sequential Reactions
Dominguez, Esteban
Carretero, Juan C.
Following an homologation sequence the readily available enantiomerically pure γ-hydroxy vinyl sulfone 2 has been transformed, with complete control of the stereochemistry, into γ-hydroxy vinyl sulfones of polypropionate structure. The four stereotriads have been prepared by stereoselective additions of organometallics to the vinyl sulfone moiety and by stereoselective reduction of β-hydroxyketones. In a similar way, these triads are the substrates for the stereoselective introduction of the fourth consecutive asymmetric center.
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