COLCHICINE IS FORMED BY PARA-PARA PHENOL COUPLING FROM AUTUMNALINE

Authors
MAIER UH ZENK MH
Citation
Uh. Maier et Mh. Zenk, COLCHICINE IS FORMED BY PARA-PARA PHENOL COUPLING FROM AUTUMNALINE, Tetrahedron letters, 38(42), 1997, pp. 7357-7360
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
42
Year of publication
1997
Pages
7357 - 7360
Database
ISI
SICI code
0040-4039(1997)38:42<7357:CIFBPP>2.0.ZU;2-H
Abstract
In order to distinguish between ortho-para and para-para phenol coupli ng in colchicine biosynthesis, [3'-(OCH3)-C-14]autumnaline was convert ed to [C-14]colchicine in seeds of Colchicum autumnale and the product was then selectively demethylated by a bacterium that exclusively dem ethylates C-3 of colchicine. The retention of the radioactive label in 3-demethylcolchicine indicates that biosynthesis proceeds through par a-para coupling. (C) 1997 Elsevier Science Ltd.