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Synthesis Based on Cyclohexadienes. 5. A New Approach to the Synthesis of a-Ring Aromatic Steroids - a Formal Total Synthesis of (+/-)-Estrone

Rao, GSRS and Devi, LU and Sheriff, U and Banerjee, DK (1992) Synthesis Based on Cyclohexadienes. 5. A New Approach to the Synthesis of a-Ring Aromatic Steroids - a Formal Total Synthesis of (+/-)-Estrone. In: Australian Journal of Chemistry, 45 (1). pp. 187-203.

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Official URL: http://www.publish.csiro.au/nid/51/paper/CH9920187...

Abstract

A new strategy for the construction of A-ring aromatic steroids which resulted in the formal total synthesis of estrone is described. Thus reaction of the adduct (9), obtained from 1-methoxy-4-methylcyclohexa-1,4-diene and acrolein, with 3-(m-methoxyphenyl)propylmagnesium bromide followed by oxidation afforded the bicyclo[2.2.2]octene derivative (14). Acid-catalysed rearrangement of (14) followed by an intramolecular Michael addition resulted in the cis tetraenone (18) which was dehydrogenated with palladium chloride to the pentaenone (22). Li/NH3 reduction of (22) gave 3-methoxy-D-homoestra-1,3,5(10)-trien-16-one (31) which has been converted into the methyl ether (37) of marrianolic acid, and its methyl ester (38).

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Commonwealth Scientific and Industrial Research Organisation Publishing.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 30 May 2011 06:00
Last Modified: 30 May 2011 06:00
URI: http://eprints.iisc.ernet.in/id/eprint/37761

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