Synthesis of steroids investigations on the total synthesis of testosterone analogues

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.