The stereoselective alkylation and conformational analysis of 15-hexadecanolide

Article abstract of DOI:10.1016/S0040-4039(00)74478-9

15-Hexadecanolide can be alkylated with 80% stereoselectivity. The stereochemistry of the major product was proven by chemical correlation with the alkylation products of cyclopentadecanone. A simple model using [4444] conformation of cyclohexadecane is proposed to rationalize these results along with molecular mechanics calculations.