Synthetic studies directed towards complex diterpenoids. Part 15. Synthesis and stereochemistry of the catalytic reduction of Δ4b(5)-gibbenes and related compounds

Ranu, Brindaban C. ; Sarkar, Manish ; Chakraborti, Prabir C. ; Ghatak, Usha Ranjan (1982) Synthetic studies directed towards complex diterpenoids. Part 15. Synthesis and stereochemistry of the catalytic reduction of Δ4b(5)-gibbenes and related compounds Journal of the Chemical Society, Perkin Transactions 1 . pp. 865-873. ISSN 0300-922X

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1982...

Related URL: http://dx.doi.org/10.1039/P19820000865

Abstract

The synthesis of, and substituent effects in the stereoselectivity of catalytic hydrogenation of, a series of methyl- or methoxy-substituted (±)-4b,9-cyclogibba-1(10a),2,4-trien-8-ones (1a-g) and (±)-gibba-1(10a), 2,4,4b(5)-tetraen-8-ones (2a-g) are described, which lead to stereocontrolled syntheses of the respective C-4b epimeric gibbanes (3a-g) and (4a-g). The key intermediate tetrahydrofluorene-2-carboxylic acids (10a-g), prepared by cycloaddition reactions, are converted into the corresponding α-diazomethyl ketones (12a-g) which are subjected to intramolecular oxo-carbenoid addition or perchloric acid-trifluoroacetic acid-catalysed cyclisation leading to the cyclopropyl ketones (1a-g) and the Δ4b(5)-gibbenes (2a-g), respectively.

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