The (–)-enantiomer (11) of the insect pheromone (+)-exo-brevicomin has been synthesized directly by hydrogenation–hydrogenolysis of the L-lyxo-nona-3,8-dienulose derivative (10). Epoxide ring opening of the methyl 3,4-anhydro-D-galactopyranoside (6), which was readily obtained from methyl α-D-glucopyranoside, permitted the required configurational inversions at C-3 and C-4
R. J. Ferrier, P. Schmidt and P. C. Tyler, J. Chem. Soc., Perkin Trans. 1, 1985, 301 DOI: 10.1039/P19850000301
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