Opioid compounds and methods for making therefor

A process for the preparation of a compound of formula (I) ##STR34## or a pharmaceutically acceptable ether, ester or salt thereof or a physiologically functional derivative thereof, wherein:

• R.sup.3, R.sup.4, R.sup.5 =hydrogen or methyl, where the total number of methyl groups is one or two;
• R.sup.6 =hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 methoxyalkyl, or C.sub.3 -C.sub.6 cycloalkyl;
• R.sup.8 and R.sup.9 may be the same or different, and may be hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.10 aryl, or C.sub.5 -C.sub.10 aryl C.sub.1 -C.sub.6 alkyl, or R.sup.8 and R.sup.9 together may form a ring of 5 or 6 atoms;
• said process comprising
• reacting a compound of formula (VI), with a phenylmetallic compound of formula (VII):
• ##STR35## wherein:
• R.sup.3 and R.sup.6 and R.sup.8 and R.sup.9 are as defined above;
• Q is a hydroxy-protecting group;
• M is a metal species;
• W is 1-benzotriazolyl or trichlorotitaniumoxy;
• deprotecting the hydroxy group;
• and
• optionally derivatizing the phenol of the resulting compound of formula (I) to provide a pharmaceutically acceptable ether, ester or salt thereof or a physiologically functional derivative thereof.