Issue 6, 1988

Synthesis of tetrahydrodicranenone B

Abstract

The naturally occurring cyclopentenone, tetrahydrodicranenone B (1J), has been synthesized from the cyclopentenone (3), prepared by Birch reduction/alkylation of 6-methoxyindanone followed by ozonolysis of the dihydroindanone (2). The lower side chain was elongated by selective addition of a five-carbon Grignard reagent to the aldehyde (6), obtained from the ester (3), to give the alcohol (7). The alcohol (7) could also be prepared from the 7-methoxyindanone (14), in which all the carbons of the lower side chain are already present, by a similar reductive alkylation/ozonolysis sequence (Scheme 3). The alcohol (7) was converted into the natural product by radical deoxygenation, followed by functional group manipulation.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 1401-1406

Synthesis of tetrahydrodicranenone B

C. J. Moody, S. M. Roberts and J. Toczeka, J. Chem. Soc., Perkin Trans. 1, 1988, 1401 DOI: 10.1039/P19880001401

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