A-homo-B,19-dinorandrostanes from 6β-methanesulfonyloxy-5-methyl-19-nor-5β-androst-9-ene derivatives

[img]PDF - Authorized users only
Language: English
564Kb
Title:A-homo-B,19-dinorandrostanes from 6β-methanesulfonyloxy-5-methyl-19-nor-5β-androst-9-ene derivatives
Creators:
Kasal, Alexander
Podlaha, Jaroslav
Zajíček, Jaroslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 5, pp. 1070-1086

Abstract

6β-Methanesulfonyloxy derivatives of 5-methyl-19-nor-5β-androst-9-enes with different oxygen functionalities in positions 3β and 17 ( compounds <i>IX</i> and <i>XVII</i>) were converted to 4a-methyleno-A-homo-B,19-dinor-5β-androst-9-ene derivatives (compounds <i>X, XX</i> and <i>XXI</i>) which were hydrogenated to give derivatives of 4aα-methyl-A-homo-5,19-dinor-5β,10α-androstane (<i>XXII, XXIII</i>) and 4aα-methyl-A-homo-B,19-dinor-5α,9β-androstane (<i>XXIV, XXV</i>). The structure of the latter compounds has been confirmed by X-ray diffraction of diketone <i>XXVII</i> which has been shown, in accordance with calculations by the MM2 method, to exist in a boat conformation of the ring C. The 17β-hydroxy-3-ketone <i>XXX</i> exhibits in vivo antiandrogenic activity.

Title:A-homo-B,19-dinorandrostanes from 6β-methanesulfonyloxy-5-methyl-19-nor-5β-androst-9-ene derivatives
Creators:
Kasal, Alexander
Podlaha, Jaroslav
Zajíček, Jaroslav
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:5
Page Range:pp. 1070-1086
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19911070UNSPECIFIED
ID Code:5025
Item Type:Article
Deposited On:22 Feb 2010 11:28
Last Modified:22 Feb 2010 10:29

Citation

Kasal, Alexander; Podlaha, Jaroslav; Zajíček, Jaroslav (1991) A-homo-B,19-dinorandrostanes from 6β-methanesulfonyloxy-5-methyl-19-nor-5β-androst-9-ene derivatives. Collection of Czechoslovak Chemical Communications, 56 (5). pp. 1070-1086. ISSN 0010-0765

Repository Staff Only: item control page