Patent ID: 6346628
Filing Date: 2002-02-12
Classification: C07D

Abstract:
A process for producing a compound of the formula (VI): wherein R is hydrogen or a hydrogen-protecting group and X is hydrogen or alkyl, and the double bond represents either an E- or Z-configuration, or a pharmaceutically acceptable salt or hydrate thereof, which comprises: propargylating a 4-mercaptophenol, and protecting the hydroxyl group of the 4-mercaptophenol, to yield a compound of the formula (II): wherein R1 is a hydroxy-protecting group; oxidizing said compound (II) to yield a compound of the formula (III): subjecting said compound (III) to a thermal rearrangement reaction to yield a compound of the formula (IV): wherein R1 is as defined above; subjecting said compound (IV) to stepwise oxidation of the hydroxymethyl group and optionally deprotecting said hydroxyl group to yield a compound of the formula (I): wherein R is as defined above, or a reactive derivative thereof; and subjecting the compound of the formula (I) or a reactive derivative thereof to the following reactions: (1) reaction with a compound of the formula (V) wherein X is hydrogen or alkyl; or (2) reaction with a compound of the formula (Vâ€²): or a salt thereof, followed by oxidation and reaction with an ylide under conditions for a Wittig reaction; and (3) optionally deprotecting said hydroxyl group.