Issue 0, 1983
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Condensed cyclic and bridged-ring system. Part 9. Stereocontrolled synthesis and X-ray structural analyses of cis-3,4,4a,9,10,10a-hexahydro-1,4a-ethanophenanthrene-2(1H),12-dione and trans-3,4,4a,9,10,10a-hexahydro-3,4a-ethanophenanthrene-2(1H), 12-dione

Gopa Sinha,   Santosh K. Maji,   Usha Ranjan Ghatak,   Monika Mukherjee (née Mondal),   Alok K. Mukherjee  and  Ajit K. Chakravarty  

Abstract

The isomeric bridged diketones cis-3,4,4a,9,10,10a-hexahydro-1,4a-ethanophenanthren-2(1H), 12-dione (5) and trans-3,4,4a,9,10,10a-hexahydro-3,4a-ethanophenanthren-2(1H),12-dione (6) have been synthesised by highly regioselective intramolecular aldol condensations through the stereochemically defined cis- and trans-2,2-ethylenedioxy-1,2,3,4,4a,9,10,10a-octahydrophenanthren-4a-ylacetaldehydes (3f) and (4f) and their structures have been established by X-ray analysis. The isomeric diketones (5) and (6) undergo cleavage with toluene-p-sulphonic acid in boiling benzene leading finally to the known keto-ester (3a) and a new spiro-keto acid (14). Carbon-13 n.m.r. spectra of these and the other compounds reported in this paper have been measured and assigned.

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Article information

DOI
https://doi.org/10.1039/P19830002519
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1983, 2519-2528

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Condensed cyclic and bridged-ring system. Part 9. Stereocontrolled synthesis and X-ray structural analyses of cis-3,4,4a,9,10,10a-hexahydro-1,4a-ethanophenanthrene-2(1H),12-dione and trans-3,4,4a,9,10,10a-hexahydro-3,4a-ethanophenanthrene-2(1H), 12-dione

G. Sinha, S. K. Maji, U. R. Ghatak, M. Mukherjee (née Mondal), A. K. Mukherjee and A. K. Chakravarty, J. Chem. Soc., Perkin Trans. 1, 1983, 2519 DOI: 10.1039/P19830002519

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