Tetrahedron

Stereoselective syntheses of deuterium labelled marmesins; valuable metabolic probes for mechanistic studies in furanocoumarin biosynthesis

V Stanjek, M Miksch, W Boland

Index: Stanjek, Volker; Miksch, Martin; Boland, Wilhelm Tetrahedron, 1997 , vol. 53, # 52 p. 17699 - 17710

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Citation Number: 22

Abstract

Stereoselective syntheses of deuterium labelled marmesins 3a-3e as metabolic probes for biosynthetic studies are described. Starting from iodo-umbelliferone (5), the title compounds were readily available by copper catalysed alkylation-cyclisation and subsequent transfer- hydrogenation of the resulting furanocoumarins 6a-6e. The bioconversion of marmesin by a microsomal preparation of A. majus yielded psoralene (4) and acetone in a single step ...

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