Resolution of methyl nonactate

A straightforward resolution of racemic methyl nonactate has been achieved by chromatographic separation of the corresponding D-mandelates followed by chemoselective hydrolysis of the mandelate ester function. Baker's yeast r eduction of the ketone derived from racemic methyl nonactate proceeded with high enantioselectivity to give (+)-8-epi-methyl nonactate and (-)-methyl nonactate as alternative building blocks for macrotetrolide synthesis but w as less efficient for the production of the latter compound. (C) 2000 Elsev ier Science Ltd. All rights reserved.