Synthesis and configuration analysis of 9,18- and 10,18-dihydroxystearic acid methyl esters

Abstract

The syntheses of 9,18- and 10,18-dihydroxystearic acid methyl esters, which are components of plant cutin, are described. Conversion of the primary alcohol group of these diols to a t-butyldimethylsilyl ether followed by reaction of the residual secondary alcohol group with ( S)-(-)-1-(1-naphthyl)ethylisocyanate produces diastereomeric carbamates that are resolved by silica gel high-performance liquid chromatography and whose configurations may be assigned by the 1H-NMR shift differences of the carbomethoxy and silylmethyl signals.