Synthetic routes to 9-azasteroids

Easom, John MM

Abstract

Syntheses of azasteroids both from natural steroids and from precursors bearing a nitrogen atom are reviewed.
The present research was directed towards the preparation of suitable tricyclic compounds possessing the future A-,B- and D-rings of a 9-azasteroid system which were suitably substituted for the construction of ring C of the azasteroid system with ring A-aromatic.
The first part of this work describes the synthesis of a tricyclic compound possessing a suitable side chain on the future D-ring for construction of the C-ring but the low yield of this compound proved prohibitive.
The second part concerns the attempted preparation of a tricyclic compound possessing an aromatic substituent on the future D-ring which was suitable for formation of the C-ring.
The last section describes the synthesis and stereochemistry of A-,B- and D-ring azasteroid precursors which possessed a substituent attached to the nitrogen atom of the future B-ring suitable for the formation of the C-ring and a leaving group attached to the future D-ring. Synthesis of the C-ring of these compounds all proved unsuccessful.

Citation

Easom, J. M. (1975). Synthetic routes to 9-azasteroids