US 4,219,489 A · Synthesis of steroids

Abstract

Method and compounds are provided for use in the synthesis of steroids wherein a polyolefin is provided having an initiating group having a chalcogen atom in juxtaposition to a double bond, so as to be capable of bond formation to close to form a ring and having a terminating group involving pi unsaturation (a double or triple bond) conjugated to an aromatic ring. Upon acid catalysis, sigma bonds are formed through the interaction of a carbocation formed at the carbon atom bonded to the chalcogen atom and the double bond intermediate the initiating group and the terminating group, which close to form rings of a steroid nucleus, the carbocation interacting with the pi unsaturation conjugated with the aromatic group and being captured by a nucleophile present in the acidic reaction medium. The resulting steroid product may then be modified in known ways to produce known steroids.

Claims8

Dependent claims

A compound of the formula ##STR16## wherein:

Ar is phenyl, naphthyl or substituted phenyl, wherein said substituent is alkyl of from 1 to 4 carbon atoms, hydroxy, thiol, alkoxy of up to 4 carbon atoms, or alkylthio of up to 4 carbon atoms.

Dependencies are inferred from the claim text.

Facts

Application

05/939,595Filed 5 Sep 1978 · continuation in part

Priority

27 Nov 1974

Granted

26 Aug 1980

Term ends

Not estimatedThe source records don’t support an estimate.

Classification32 codes

C07J 61/00
Steroids in which the cyclopentahydrophenanthrene skeleton has been modified by contraction of
C07C 29/00
Preparation of compounds having hydroxy or o-metal groups bound to a carbon
C07C 29/103
Of ethers, including cyclic ethers, e.g. oxiranes: of cyclic ethers
C07C 29/147
Of >C=O containing groups, e.g. —COOH: of carboxylic acids or derivatives thereof

Synthesis of steroids

Life of this patent

Synthesis of steroids

Life of this patent

Abstract

Claims8