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Studies in stereochemistry—I : Stereospecific routes to trans- anti- and cis- syn-Δ8-dodecahydrophenanthrenes

Balasubramanian, SK (1961) Studies in stereochemistry—I : Stereospecific routes to trans- anti- and cis- syn-Δ8-dodecahydrophenanthrenes. In: Tetrahedron, 12 (4). pp. 196-204.

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Official URL: http://dx.doi.org/10.1016/0040-4020(61)80034-3

Abstract

Reduction of trans-1-oxo-7-methoxy-1,2,3,4,9,10,11,12-octahydrophenanthrene (XI) by lithium tri-t-butoxyaluminohydride gave trans-1β-hydroxy-7-methoxy-1,2,3,4,9,10,11,12-octahydrophenanthrene (XII) which on lithium-liquid ammonia reduction gave trans-anti-1β-hydroxy-7-oxo-Δ8(14)-dodecahydrophenanthrene (XIII). Reduction of cis-1-oxo-7-methoxy-1,2,3,4,9,10,11,12-octahydrophenanthrene (XV) by sodium borohydride gave cis-1α-hydroxy-7-methoxy-1,2,3,4,9,10,11,12-octahydrophenanthrene (XVI) which on lithium-liquid ammonia reduction gave cis-syn-1α-hydroxy-7-oxo-Δ8(14)-dodecahydrophenanthrene (XVII).

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 23 Jun 2010 09:56
Last Modified: 19 Sep 2010 06:09
URI: http://eprints.iisc.ernet.in/id/eprint/28437

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