Investigations on the total synthesis of testorterone and its isomers : A thesis submitted to the I.I.Sc. for the degree of doctor of philosophy.

Abstract

The thesis entitled "Investigations on the Total Synthesis of Testosterone and its Isomers" is divided into two parts. Part I consists of a comprehensive review of the earlier work done on the chemistry of testosterone and its isomers. Part II is divided into two sections: A and B. In Section A, the total synthesis of 8-isotestosterone as well as our unsuccessful attempts to convert the same to testosterone is recorded. This section also contains the synthesis of another isomer of testosterone which has been tentatively assigned the structure of 9-iso-10-isotestosterone. Section B consists of our successful reinvestigations on the metal-ammonia-alcohol reduction of trans-18-hydroxy-8-methyl-4,5-(3'-methyl-4'-methoxybenzo)-hydrindane leading to the syntheses of 17?-benzoyloxy-des-A-androst-5-en-3-one and 17?-benzoyloxy-des-A-androstan-5-one. These are valuable intermediates for the synthesis of steroids in general and testosterone in particular.