Stereoselective syntheses of deuterium labelled Marmesin (cas 13710-70-8)s; valuable metabolic probes for mechanistic studies in furanocoumarin biosynthesis

Add time:09/09/2019    Source:sciencedirect.com

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 and proceeded as a syn-elimination of the alkoxy-substituent together with a single hydrogen atom from a vicinal carbon atom (β-cleavage).

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