Ring-c aromatic steroids. 17β-Methyl-18-norpregna-8,11,13-trienes
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 1048-1055
- https://doi.org/10.1039/p19790001048
Abstract
Boron trifluoride–diethyl ether converts 20α,21-diacetoxy-9α,11α-epoxy-17α-hydroxypregn-4-en-3-one (18) into 20α,21-diacetoxy-17β-methyl-18-norpregna-4,8,11,13-tetraen-3-one (19). An analogous C-aromatic steroid is similarly obtained from 9α,11α-epoxy-17α-methyltestosterone (9). From (19), by modifications of ring A and the 17α-side-chain, a series of 17β-methyl C-aromatic steroids has been prepared. The 5β configuration of the 3-ketone (21), obtained stereospecifically by hydrogenation of the Δ4-3-ketone (19) is deduced from 13C and 1H n.m.r. data. Some acid-catalysed transformations of 17α-methyl-Δ9(11)-testosterone (1) are reported.This publication has 2 references indexed in Scilit:
- Chemistry of the podocarpaceae—XVTetrahedron, 1968
- A simple route to steroid 17α,20α,21-triols and their 21-monoestersTetrahedron, 1965