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.