Total syntheses of (+)- and (–)-nonactate esters using silicon compounds to control the stereochemistry
Abstract
1,3-Transposition, using the epoxidation of the allylsilane 7, derived from the meso 3,4-disilylated adipate 1, gives the 1,4-related stereocentres of 8-oxo-6-hydroxy-3-dimethyl(tolyl)silylnonanoic acid ethylene acetal 10; two highly stereocontrolled sequences from this common intermediate give methyl (+)-nonactate 13 and benzyl (–)-nonactate 17.