CHEMOENZYMATIC SYNTHESIS OF THE MORPHINE SKELETON VIA RADICAL CYCLIZATION AND A C-10-C-11 CLOSURE

Authors
BUTORA G HUDLICKY T FEARNLEY SP GUM AG STABILE MR ABBOUD K
Citation
G. Butora et al., CHEMOENZYMATIC SYNTHESIS OF THE MORPHINE SKELETON VIA RADICAL CYCLIZATION AND A C-10-C-11 CLOSURE, Tetrahedron letters, 37(45), 1996, pp. 8155-8158
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
45
Year of publication
1996
Pages
8155 - 8158
Database
ISI
SICI code
0040-4039(1996)37:45<8155:CSOTMS>2.0.ZU;2-P
Abstract
A short synthesis of a morphinan skeleton has been accomplished. The k ey steps involve enzymatic dihydroxylation of beta-bromoethyl benzene, vinyl and aryl radical cyclizations, and Friedel-Crafts closure of an aziridinium ion or an acid-catalyzed closure of an aldehyde to form t he C-10-C-11 bond. Copyright (C) 1996 Elsevier Science Ltd