Scalable Total Synthesis of Piceatannol-3′-O-β-d-glucopyranoside and the 4′-Methoxy Congener Thereof: An Early Stage Glycosylation Strategy

Abstract

Scalable syntheses of piceatannol-3′-O-β-d-glucopyranoside and the 4′-methoxy congener thereof were achieved. This route features an early implemented Fischer-like glycosylation reaction, a regioselective iodination of phenolic glycoside under strongly acidic conditions, a highly telescoped route to access the styrene derivative, and a key Mizoroki–Heck reaction to render the desired coupled products in high overall yield.

Key words

piceatannol - glycosides - Mizoroki–Heck reaction - Fischer glycosylation - carbohydrate chemistry

Publication History

Received: 12 July 2021

Accepted after revision: 07 September 2021

Accepted Manuscript online:
07 September 2021

Article published online:
21 October 2021

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