• D K Banerjee

      Articles written in Journal of Chemical Sciences

    • Chiral synthesis of optically active S(+)-2,6,7,7a-tetrahydro-1β-hydroxy-4-formyl-7aβ-methylindene

      D K Banerjee T R Kasturi A Sarkar

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      The chiral aldol cylization of the prochiral triketone 3 using l-valine afforded the optically active compound 4 in high chemical and optical yield. The configuration and optical purity of (+)4 was determined by ORD, chemical resolution andnmr chirallsr studies. The title compound (+)7 was prepared from (+)4 following our earlier reported procedure.

    • Contributions to organic synthesis and reaction mechanisms

      D K Banerjee

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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.

    • Investigations towards the synthesis of a CD-steroid intermediate

      D K Banerjee T R Kasturi R Sai Baba A Sarkar

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      The development of a new synthesis of 2,6,7,7a-tetrahydro-lβ-hydroxy-4-formyl-7a-methylindene was undertaken involving the preparation of 2,6,7,7a-tetra-hydro-1β-hydroxy-4-methoxymethyl-7a-methylindene because of the erratic yield in the last oxidation step of the reported synthesis of the former compound. Although various attempts to prepare the latter were not successful, interesting rearrangement products, the dienone, 5,6,7,7a-tetrahydro-4,7a-dimethyl-5H-indene-1,5-dione and the tricyclic keto alcohol, 2,6-diketo-3-methyltricyclo(5,2,1,0)decan-8-ol, were obtained, the structures of which have been proved by spectral data. Mechanisms for the formation of these products have been proposed.

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