Enantiomeric synthesis of (3R)-3-amino-5-methyl-2-oxo-hexan-1-ol hydrochloride from cyclohexylideneglyceraldehyde

Abstract

The first enantioselective synthesis of the title compound, (3R)-3-amino-5-methyl-2-oxo-hexan-1-ol hydrochloride (9a), an inhibitor of metalloprotein aminopeptidases has been developed from an enantiomerically pure 3-alkylglycerol. The required 3-alkylglycerol was, in turn, prepared by simple Grignard addition to cyclohexylideneglyceraldehyde 1 followed by separation of the epimeric product carbinols by normal column chromatography. The other attractive features of the synthesis was the use of inexpensive reagents and operationally simple synthetic protocols.