Synthese totale de la (d, l). ALPHA.-conidendrine.

Y Nabi, R Dhal, E Brown

Index: Nabi, Yahia; Dhal, Robert; Brown, Eric Chemistry Letters, 1983 , p. 1543 - 1546

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Abstract

Michael addition of the carbanion of the dithian 7 (derived from O-benzyl vanillin) on butenolide, afforded the saturated lactone 8. Alkylation of the latter with the benzylic bromide 6, followed by regeneration of the carbonyl group gave the α, β-disubstituted lactone 10. Reduction of the ketonic carbonyl group of compound 10 using NaBH 4, followed by treatment with CF 3 CO 2 H and catalytic hydrogenolysis afforded (d, l) α-conidendrin 1.