An efficient synthesis of trans- gamma -oxo- alpha , beta -unsaturated carboxylic acids, the intermediates for patulolide A and pyrenophorin

Davis, K.J.; Bhalerao, U.T.; Rao, B.V.

Indian Journal of Chemistry. Sect. B 40(8): 656-661


ISSN/ISBN: 0376-4699
Accession: 003357003

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The efficient syntheses of 11,benzyloxy-4-oxo-2-(E)-dodecenoic acid and 7-benzyloxy-4-oxo-2-octenoic acid, the important precursors of the macrolide antifungals patulolide A and pyrenophorin, respectively, are described. The key steps involved in the synthesis include: (1) the coupling of the alkyl lithium with alpha , beta -unsaturated aldehyde, and (2) the oxidation of the cis-trans mixture of gamma -oxo- alpha , beta -unsaturated aldehyde to the trans- gamma -oxo- alpha , beta -unsaturated carboxylic acid.