PREPARATION OF ENANTIOMERICALLY PURE 1-HYDROXY-NEOCEMBRENES TO DETERMINE THE UNSOLVED ABSOLUTE CONFIGURATION OF CEMBRENOIDS

Article abstract of DOI:10.1246/cl.1983.1121

Cis and trans 1-hydroxy-neocembrenes were prepared in an enantiomerically pure form by reduction of dl-ketone with respective (+)- and (-)-Darvon-LiAlH4 complex followed by purification with the aids of esterification with d- and l-menthoxyacetyl chlorides and (-)-camphanic acid chloride, respectively.Absolute configuration of naturally occurring (+)-mayol and (+)-cembrenene was determined by correlation with enantiomerically pure compounds.