Chiral Sulfoxides as Building Blocks for Enantiopure 1,3-Diol Precursors in the Synthesis of Natural Products
Claude Bauder, Jean Martínez and Xavier J. Salom-Roig
Pages 885-902 (18)
1,3-Diol motif is of particular interest due to its prominence within many classes of natural products. In this field, β,δ-diketo
sulfoxides are specially attractive because both syn- and anti-1,3-diols can be prepared from these key compounds by two successive high
diastereoselective reductions of both carbonyls. Thus, β-carbonyl reduction requires DIBAL-H or the ZnX2/DIBAL-H system. The resulting
stereochemistry of the corresponding hydroxyl is fully controlled by the chiral sulfoxide group. Then, the reduction of δ-carbonyl
leads to syn or anti 1,3-diols depending on the hydride reagents employed and the stereoselectivity is directed by the newly formed β-
hydroxylic center. In this paper, emphasis is given to the use of valuable β,δ-diketo sulfoxides in the total synthesis of selected natural
1, 3-Diols, asymmetric synthesis, chiral sulfoxides, synthetic methods, total synthesis.
Laboratoire de Chimie Biomimetique des Metaux de Transition, Institut de Chimie, UMR CNRS 7177, Universite de Strasbourg, 4, rue Blaise Pascal, B. P. 1032, 67070 Strasbourg cedex, France.