Helvetica chimica acta

Synthese von orellin

HA Hasseberg, H Gerlach

Index: Hasseberg, Hans-Albrecht; Gerlach, Hans Helvetica Chimica Acta, 1988 ,  vol. 71, p. 957 - 963

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Citation Number: 22

Abstract

Orelline (l), a metabolite of the toadstool Cortinurius Orellunus FRIES with 2, 2'-bipyridine structure, has been synthesized by the following method. The easily accessible 2-bromo-3- hydroxypyridine (3) was converted into the corresponding [2-(trimethylsilyl) ethoxy] methyl (SEM) ether 4 and coupled with Zn and NiCI,/Ph, P to form the bipyridine derivative 5 in 79% yield. Due to the chelating effect of the two SEM-ether groups in 5, it was possible to form ...