Synthesis of all the four possible stereoisomers of acaterin, naturally occurring ACAT inhibitor, and the determination of its absolute configuration

Article abstract of DOI:10.1016/0040-4020(95)00303-P

Enantioselective synthesis of all the possible stereoisomers of acaterin 1, naturally occurring ACAT inhibitor with acetogenin-type skeleton, was accomplished starting from both the enantiomers of ethyl 3-hydroxy butanoate 3. Stereochemistry of synthetic samples 1 and pseudo-1 was unambiguously assigned by converting to the authentic compound. The absolute configuration of natural acaterin was determined as (4R, 1'R) by careful comparison of TLC behavior and spectral and optical data.