Enantiomeric synthesis of (3R)-3-amino-5-methyl-2-oxo-hexan-1-ol hydrochloride from cyclohexylideneglyceraldehyde
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.
Sharma
A
Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai, India.
Chattopadhyay
S