Steroid 19,B-dinor-8,10-iso-analogues

Abstract

The Birch reduction of 3-methoxy-B-nor-8-isoestra-1,3,5(10)-trienes followed by acid hydrolysis produces steroid androgen 19,B-dinor-8,10-iso-analogues. By means of X-ray analysis and correlation NMR spectroscopy of 16,16-dimethyl-D-homo-19,B-dinor-8-isotestosterone, C(20)H(30)O(2), it is demonstrated that the main conformations in the crystal and in solution for two 19,B-dinor-8,10-iso-analogues are, in general, the same.

17β-Ethoxy-3-methoxy-8-isoestra-1,3,5(10)-triene

“…Ring D (C13±C17) has an almost regular 13-envelope conformation, with an angle between the C14/C15/C16/C17 (base of the envelope) and C13/C14/C17 planes of 46.7 (1) . The molecule is approximately`¯at' compared with the B-nor-8-iso-analogue (Egorov et al, 2002); the plane of the aromatic ring makes an angle of 43.1 (2) with the`chair bottom' of ring C and an angle of 32.3 (2) with the base of the envelope of ring D. The O1Á Á ÁO2 distance, which is known to be important for binding to an estrogen receptor, is 10.916 (5) A Ê .…”

Recent Developments in the Isolation and Synthesis of D‐Homosteroids and Related Compounds

“…61 An NMR study has been performed on the stereo-structure and intramolecular dynamics of D-homoandrostenes and a B-nor-8-iso-D-homoestrone derivative. 62 The crystal structures of two steroid 19,B-dinor-8,10-iso analogs 63 and of two 6-oxa-D-homo-8-isoestra derivatives 64 have been published. An investigation has been made on the phosphorescence of enaminocarbonyl-8-azasteroids (including D-homo derivatives).…”