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Issue 7, 1976
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Synthetic studies on terpenoids. Part XVIII. Stereocontrolled synthesis of (±)-1,2,3,4,4a,9,10,10aα-octahydro-1α-methylphenanthrene-1β,4aβ-dicarboxylic acid and the 7-methoxy-analogue: a potential intermediate for diterpenoid syntheses

Abstract

A stereocontrolled synthetic route to (±)-1,2,3,4,4a,9,10,10aα-octahydro-1α-methylphenanthrene-1β,4aβ-di-carboxylic acid (Ia) and the 7-methoxy-analogue (Ib) is described. The present approach differs basically from earlier ones and proceeds through polyhydrobenzindenone intermediates. 2,3,4,5-Tetrahydro-3-methylbenz[e] inden-1-one (Va) and the corresponding 7-methoxy-compound (Vb) were transformed through several steps into cis-9b-acetonyl-3a,4,5,9b-tetrahydro-3-methylbenz[e]inden-1-one (XIIIa) and its methoxy-derivative (XIIIb). These unsaturated diketones underwent intramolecular Michael condensation, affording tetracyclic bridged ketones (XIVa and b), which were converted into the acids (Ia and b). In the methoxy-series, disproportionation of a polyhydrobenzindenone derivative was noted.

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Article type: Paper
DOI: 10.1039/P19760000722
J. Chem. Soc., Perkin Trans. 1, 1976, 722-727

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    Synthetic studies on terpenoids. Part XVIII. Stereocontrolled synthesis of (±)-1,2,3,4,4a,9,10,10aα-octahydro-1α-methylphenanthrene-1β,4aβ-dicarboxylic acid and the 7-methoxy-analogue: a potential intermediate for diterpenoid syntheses

    A. S. Sarma, A. K. Banerjee and P. C. Dutta, J. Chem. Soc., Perkin Trans. 1, 1976, 722
    DOI: 10.1039/P19760000722

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