Synthesis and Reactions of Optically Active 1,3-Diols

The ‘syn’-1,3-diols 3 , 4 and 5 with a C₇, C₆, and C₅ chain, respectively, were synthesized from methyl hydrogen 3-hydroxyglutarate ( 2 ; Schemes 1 and 2). The latter is available in (R)- and (S)-configuration. Octyl (3R)-4-chloro-3-hydroxybutanoate ( 17 ) is an alternative starting material for the preparation of 5 (Scheme 3.) The epoxide 20 , derived from 5 in a one-pot reaction, is a versatile synthon, which selectively reacts with a great number of nucleophiles (Scheme 4).