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Total syntheses of substituted hydrobenz[e]indenes and hydrophenanthrenes

Banerjee, DK and Kasturi, TR and Purushotham, V (1984) Total syntheses of substituted hydrobenz[e]indenes and hydrophenanthrenes. In: Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 23 (5). pp. 395-411.

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Abstract

A new method, involving addition of $3-MeOC_6H_4CR:CH_2$ (R=$CO_2$Et, cyano) to, or condensation of $3-MeOC_6H_4CH(CN)CH_2R_1$ $(R_1=Br, Cl)$ with, diones I (n=1, 2) and Et Me 3-oxoadipate, has been developed for the synthesis of benz[e]indenone II, benz[e]indenes III and methylphenanthrenes IV as precursors for the synthesis of steroids and D-homosteroids. For the preparation of II-IV, a variety of conditions for the Michael addn. or alkylation have been studied. The benz[e]indene V and phenanthrenes , i.e. VI, could be satisfactorily prepared by further elaboration of these products. Catalytic hydrogenation of the styrene double bond in V and VI invariably leads to a mixture of cis- and trans-isomers, the cis-isomer predominating in the hydrobenz[e]indenes, and the trans-isomer predominating in hydrophenanthrenes. This is contrary to expectations of the stereoselective formation of the trans-fused ring systems in accordance with the general observation in the hydrogenation of 3,3a,4,5-tetrahydrobenz[e]indenones and 1,2,3,9,10,10a-hexahydrophenanthrenes with an angular Me group at C-3a and C-10a respectively. The formation of a mixture of cis- and trans-isomers is due to the presence of the substituent (cyano or carbomethoxyl) in these compounds.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to National Institute of Science Communication and Information Resources, CSIR.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 12 May 2008
Last Modified: 27 Aug 2008 13:22
URI: http://eprints.iisc.ernet.in/id/eprint/13931

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