| dc.description.abstract | The thesis entitled “Synthesis of Steroids” is divided into two chapters with an appendix at the end. The first chapter is a literature review on testosterone and its analogues. The second chapter deals with the synthetic approach towards 8-iso-19-nortestosterone and its anthracene analogues.
The first section of this chapter concerns the conversion of trans-13-hydroxy-5-methyl-4,5-(4'-methoxybenzo)-hydroindane (I) to 1^2-(3'-acetoxycyclopentano)-2-methyl-6-keto-decahydronaphthalene (II) through five steps, viz., demethylation, diacetylation, partial deacetylation, high-pressure hydrogenation, and oxidation.
In the second section, studies on cis-2-decalone as a model compound for the fabrication of ring A have been discussed. It has been shown that direct condensation of methyl vinyl ketone with cis-2-decalone takes place in a linear fashion to give 2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydroanthracene-2-one (III).
In the last section of this chapter, it has been shown that formylation of the keto-acetate (II) takes place at C7. This section also deals with the synthesis of 1,2-(3'-hydroxycyclopentano)-2-methyl-7-keto-1,2,3,4,5,6,7,8,9,10,10a-dodecahydroanthracene (IV) and its ethylenic isomer (V). The attempts made to prepare 8-iso-19-nortestosterone have also been discussed.
The appendix of the thesis is connected with a model experiment carried out with 2-octalone-2 for the construction of ring A of steroids. | |
