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

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

Volume: 10 Issue: 6

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

Affiliation:

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.

Cite this article as:

Bauder Claude, Martínez Jean and Salom-Roig J. Xavier, Chiral Sulfoxides as Building Blocks for Enantiopure 1,3-Diol Precursors in the Synthesis of Natural Products, Current Organic Synthesis 2013; 10 (6) . https://dx.doi.org/10.2174/157017941006140206103254