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

✍ Scribed by Volker Stanjek; Martin Miksch; Wilhelm Boland

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 906 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)10237-x

✦ Synopsis

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 6&e. The bioconversion of marmesin by a microsomal preparation of A. majus yielded psoralene (4) and acetone in a single step and proceeded as a +m-elimination of the alko.xy-substituent together with a single hydrogen atom from a vicinal carbon atom @cleavage). 0 1997 Elsevier Science Ltd.

Introduction.-One of the most intriguing and least understood enzymatic reactions is the oxidative cleavage of carbon-carbon single bonds leading to olefinic products and a carbonyl compound (COz, HCOOH and HCHO).