SYNTHESIS AND CONFIGURATION ANALYSIS OF 9,18-DIHYDROXYSTEARIC AND 10,18-DIHYDROXYSTEARIC ACID METHYL-ESTERS

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 f ollowed by reaction of the residual secondary alcohol group with (S)-( -)-1-(1-naphthyl)ethylisocyanate produces diastereomeric carbamates th at are resolved by silica gel high-performance liquid chromatography a nd whose configurations may be assigned by the H-1-NMR shift differenc es of the carbomethoxy and silylmethyl signals.