Tetrahedron

A Synthetic Approach to 3-Hydroxy 4-Substituted Carboxylic Acids based on the Stereoselective Reduction of 1-Trimethylsilyl-1-alkyn-3-ones

C Alemany, J Bach, J Garcia, M López, AB Rodrı́guez

Index: Alemany, Carme; Bach, Jordi; Garcia, Jordi; Lopez, Marta; Rodriguez, Ana B. Tetrahedron, 2000 , vol. 56, # 47 p. 9305 - 9312

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Citation Number: 18

Abstract

The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3- ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C (3) stereocenter. This strategy has been applied to the synthesis of (3S, 4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc- ...