A novel stereoselective synthesis of (−)-β-conhydrine from ( R)-2,3- O-cyclohexylidine glyceraldehyde

Abstract

A novel stereoselective synthesis of (−)-β-conhydrine is achieved. Stereoselective Grignard reaction of ( R)-2,3- O-cyclohexylidine glyceraldehyde with ethyl magnesium bromide, chelation controlled stereoselective Grignard reaction of allyl imine derivative with allyl magnesium bromide, and ring-closing metathesis (RCM) of the diallyl product provides (−)-β-conhydrine in high yield.