Login

Journal Image
Current Organic Synthesis
ISSN (Print): 1570-1794
ISSN (Online): 1875-6271
VOLUME: 10
ISSUE: 6
DOI: 10.2174/157017941006140206103254      Price:  $58









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

img
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.