Approaches to the total synthesis of steroids

Abstract

The thesis is divided into two chapters. Chapter I – Section B describes the work done independently by the author. The rest of the work was carried out under the guidance of Professor D.K. Banerjee. Chapter I: The Hydrochrysenic Approach to the Steroid Synthesis Section A: A review of the earlier work is presented in this section. Section B: In this section, the preparation of trans-9?,11?-hydroxy-7-oxo-3(14)-dodecahydrophenanthrone and cis-9?,11?-hydroxy-7-oxo-dodecahydrophenanthrene is described. Section C: Attempts towards the synthesis of trimethoxy-7-oxo-3,5,6,10b,11a,12a-dodecahydrohydrochrysenic starting from 7-methoxy-1,2,5,12-tetrahydrophenanthrene are described in this section. Section D: Some model experiments on the addition of the ring-A of steroids are described. A new reagent, 1-bromobutan-1-one-3-ethylene ketal, has shown to be useful for this purpose. Chapter II: The Benzohydrindane Approach to the Steroid Synthesis The synthesis of trans-1?-hydroxy-?-2-methyl-4,5-(3'-methyl-4'-hydroxybenzo)-hydrindane, an intermediate for the synthesis of cis-isotestosterone, has been described. Attempts to reduce trans-1?-hydroxy-?-2-methyl-4,5-(3'-methyl-4'-acetoxybenzo)-hydrindane by the metal-ammonia procedure are reported. The melting point of trans-1-oxo-?-2-methyl-4,5-(3'-methyl-4'-acetoxybenzo)-hydrindane reported earlier from our laboratory has been corrected.