Synthetic investigations on testerone and its analogues—I *1: The total synthesis of 8-isotestosterone and its anthracene analogue

Banerjee, DK and Paul, V and Balasubramanina, SK and Murthy, PS (1964) Synthetic investigations on testerone and its analogues—I *1: The total synthesis of 8-isotestosterone and its anthracene analogue. In: Tetrahedron, 20 (11). pp. 2487-2498.

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Abstract

The total synthesis of 8-isotestosterone (II) and the corresponding anthracene analogue (III) following the benzohydrindane route is reported. Catalytic hydrogenation of trans-1β-acetoxy-8-methyl-4,5-(3′-methyl-4′-hydroxybenzo)-hydrindane (V) followed by oxidation has furnished two isomeric tricyclic keto acetates, viz. 1β,2α-(3′-acetoxycyclopentano)-2,5-dimethyl-6-keto-1α,2,3,4,4aα,-5α,6,7,8,8aα-decahydronaphthalene (VII) and 1β,2α-(3′-acetoxycyclopentano)-2,5-dimethyl-6-keto-1α,2,3,4,4aβ,5,6,7,8,8aβ-decahydronaphthalene (IX) which are cis-non-steroid and cis-steroid configurations of the same cyclopentano-cis-decalins. A difference in the direction of enolization of the keto acetate (VII) in alkylation reaction and enol acetylation towards the methine and the methylene carbon atoms respectively has been observed.

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier Science
Additional Information:	Copyright of this article belongs to Elsevier Science.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	20 May 2010 09:52
Last Modified:	19 Sep 2010 06:07
URI:	http://eprints.iisc.ac.in/id/eprint/27972

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