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1979•Chemistry LettersRequires access

SYNTHESES OF (±)-WARBURGANAL AND (±)-ISOTADEONAL

Akio Ohsuka, Akira Matsukawa

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Abstract

Abstract Methyl (±)-9-epidrimenate was oxidized with selenium dioxide at C-12 to give an aldehyde ester. The aldehyde group was protected by formation of an acetal, and then the methoxycarbonyl group was transformed into a formyl group. Hydrolysis of the acetal group gave (±)-isotadeonal. Stereoselective oxidation of the enolate generated from (±)-isotadeonal monoacetal gave (±)-warburganal monoacetal, which was hydrolyzed to (±)-warburganal.

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Abstract Methyl (±)-9-epidrimenate was oxidized with selenium dioxide at C-12 to give an aldehyde ester. The aldehyde group was protected by formation of an acetal, and then the methoxycarbonyl group was transformed into a formyl group. Hydrolysis of the acetal group gave (±)-isotadeonal. Stereoselective oxidation of the enolate generated from (±)-isotadeonal monoacetal gave (±)-warburganal monoacetal, which was hydrolyzed to (±)-warburganal.

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Available abstract

Abstract Methyl (±)-9-epidrimenate was oxidized with selenium dioxide at C-12 to give an aldehyde ester. The aldehyde group was protected by formation of an acetal, and then the methoxycarbonyl group was transformed into a formyl group. Hydrolysis of the acetal group gave (±)-isotadeonal. Stereoselective oxidation of the enolate generated from (±)-isotadeonal monoacetal gave (±)-warburganal monoacetal, which was hydrolyzed to (±)-warburganal.

Key concepts: Chemistry

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