An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-D-glucopyranoside

Abstract

A seven-step and scalable synthesis of dihydronorcapsaicin β-D-glucopyranoside, non-pungent and adrenal secretion enhancement activity (diet effect), was accomplished from vanillin. A simple and inexpensive glucosyl donor, acetobromoglucose, was reacted with phenolic hydroxyl group of a-iodovanillin nitrile under basic conditions. Another key step was the lipase-catalyzed coupling reaction of primary amine, which was resulted from the reduction of the glucosylated product, with methyl nonanoate.