Abstract
A stereoselective route to (±)-methyl homononactate (4b) and (±)-methyl 8- epi-homononactale (5b), synthetic precursors to the antibiotic tetranactin, is presented. Key steps involve employing the regioseleclive ring opening of l-(benzyloxy)but-3-ene oxide (8) with the dianion derived from methyl(2-methyl, 3-oxo)butanoate (9), and the stereoselective addition of dialkyl zinc species to a β-alkoxyaldehyde precursor (6). Conditions have been developed to enable the diethyl zinc addition to give either isomer with reasonable selectivity.
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