A NEW AND EFFICIENT SYNTHESIS OF THE MU-SELECTIVE OPIOID ANTAGONIST CYPRODIME

Authors
KRASSNIG R SCHMIDHAMMER H
Citation
R. Krassnig et H. Schmidhammer, A NEW AND EFFICIENT SYNTHESIS OF THE MU-SELECTIVE OPIOID ANTAGONIST CYPRODIME, Heterocycles, 38(4), 1994, pp. 877-881
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
38
Issue
4
Year of publication
1994
Pages
877 - 881
Database
ISI
SICI code
0385-5414(1994)38:4<877:ANAESO>2.0.ZU;2-3
Abstract
The mu-selective opioid antagonist cyprodime has been prepared in a si x-step sequence starting from naltrexone. The 3-hydroxy group of naltr exone was removed via tetrazolyl ether (3) which was hydrgenenated cat alytically to give pylmethyl-4,5alpha-epoxy-14-hydroxymorphinan-6-one (4). Methylation gave 7-didehydro-4,5alpha-epoxy-6,14-dimethoxymorphin an (5) and hydrolysis of it ylmethyl-4,5alpha--epoxy-14-methoxymorphin an-6-one (6). Reductive opening of the 4,5-epoxy bridge and methylatio n of the resulting phenol (7) yielded cyprodime (1).