Tetrahedron letters

Colchicine is formed by para-para phenol coupling from autumnaline

UH Maier, MH Zenk

Index: Maier, Ulrich H.; Zenk, Meinhart H. Tetrahedron Letters, 1997 , vol. 38, # 42 p. 7357 - 7360

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Citation Number: 12

Abstract

In order to distinguish between ortho-para and para-para phenol coupling in colchicine biosynthesis,[3′-O14CH3] autumnaline was converted to [14C] colchicine in seeds of Colchicum autumnale and the product was then selectively demethylated by a bacterium that exclusively demethylates C-3 of colchicine. The retention of the radioactive label in 3- demethylcolchicine indicates that biosynthesis proceeds through para-para coupling.