Current Organic Synthesis

Eduardo A. Castro
Universidad Nacional de La Plata
Buenos Aires
Argentina

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

Author(s): Claude Bauder, Jean Martínez and Xavier J. Salom-Roig

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.

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

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.

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Article Details

VOLUME: 10
ISSUE: 6
Page: [885 - 902]
Pages: 18
DOI: 10.2174/157017941006140206103254