Title:
NOVEL PREPARATION METHOD OF 6BETA*77METHYLENEE33OXOO44 ENNSTEROID
Document Type and Number:
Japanese Patent JPS52122356
Kind Code:
A
Abstract:
The invention provides a novel general process for the manufacture of 6 beta ,7-methylene-3-oxo-4-ene-steroids by successively (a) reacting a 3 xi ,5 beta -dihydroxy-6-ene-steroid which is optionally etherified or esterified in the 3-position with a zinc/copper-methylene iodide reagent to introduce the 6 beta ,7-methylene bridge, (b) liberating an etherified or esterified 3-hydroxyl group if such a group is present, (c) treating the resultant 6 beta ,7-methylene-3 xi ,5 beta -dihydroxy-steroid with an oxidizing agent to dehydrogenate the 3-hydroxyl group to the oxo group, and (d) dehydrating the 6 beta ,7-methylene-5 beta -hydroxy-3-oxo-steroid to form the 4,5-double bond. The starting materials, which form a novel class of compounds, can be obtained by a novel process by converting a 5 beta ,6-oxido-3 xi -hydroxy-steroid with a selenol, for example phenylselenol, to a 6 alpha -alkyl- or arylseleno-3 xi ,5 beta -dihydroxy-steroid, oxidizing this compound with a peroxidic reagent, for example hydrogen peroxide, in a weakly acid medium to give the corresponding 6-selenonyl compound, and converting this compound, preferably by treatment with a base, preferably with 1,5-diazabicyclo[4,3,0]non-5-ene, to give the 3 xi ,5 beta -dihydroxy-6-ene-steroid. During the course of these reactions, the 3-hydroxyl group is preferably temporarily protected by esterification or etherification.
Inventors:
PEETA BUIIRANTO
Application Number:
JP3860277A
Publication Date:
October 14, 1977
Filing Date:
April 06, 1977
Export Citation:
Assignee:
CIBA GEIGY AG
International Classes:
A23K1/165; B60K17/22; C07C45/00; C07C69/013; C07C49/587; C07C67/00; C07J21/00; C07J51/00; C07J53/00; C07J63/00; C07J71/00; F16F15/14; (IPC1-7): A23K1/00; C07J1/00; C07J63/00