Journal of Organic Chemistry 2006-09-29

De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy.

Md Moinuddin Ahmed, Matthew S Mortensen, George A O'Doherty

Index: J. Org. Chem. 71 , 7741, (2006)

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Abstract

The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73-97% ee).