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Contributions to organic synthesis and reaction mechanisms

Banerjee, DK (1984) Contributions to organic synthesis and reaction mechanisms. In: Journal of Chemical Sciences, 93 (4). pp. 503-529.

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Development of new methods, leading to the first stereo-specific total synthesis of a steroid,viz equilenin, and of estrone and their derivatives and of several important synthones, useful for the preparation of physiologically active steroids, and the first conversion of an equilenane to estrane have been described. An account of the achievement of original syntheses of testosterone and its isomers and derivatives and degradation products, urinary steroids, terpenes and their important degradation products has been given. Mechanisms of Dieckmann cyclization, a novel dehydrogenation-addition reaction involving abietic acid and tetrachloro-o-benzoquinone, a rearrangement involving a substitution of cyclopentanone-2-carboxylic ester have been elucidated. An abnormaluv absorption exhibited by saturated 1,2-dicyano esters has been rationalized. Divergences in theord data of testosterone and 19-nortesto-sterone from their isomers have been explained by x-ray crystallographic studies of 8-isotestosterone, 8-iso-10-isotestosterone and 8-iso-10-iso-19-nortestosterone. A tentative explanation for the difference in their physiological activities has been suggested.

Item Type: Journal Article
Publication: Journal of Chemical Sciences
Publisher: Springer
Additional Information: Copyright for this article belongs to Springer.
Keywords: Synthesis; steroids; terpenes; reaction mechanism.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 25 Jan 2010 10:16
Last Modified: 19 Sep 2010 05:44
URI: http://eprints.iisc.ac.in/id/eprint/22979

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