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Chiral Sulfoxides as Building Blocks for Enantiopure 1,3-Diol Precursors in the Synthesis of Natural Products

[ Vol. 10 , Issue. 6 ]

Author(s):

Claude Bauder, Jean Martínez and Xavier J. Salom-Roig   Pages 885 - 902 ( 18 )

Abstract:


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 products.

Keywords:

1, 3-Diols, asymmetric synthesis, chiral sulfoxides, synthetic methods, total synthesis.

Affiliation:

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.



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