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

Jianfeng Li; Xiaoting Wang; Rong-Ping Zhang; Lei Chen

doi:10.1055/a-1639-0648

Synthesis, Table of Contents

Synthesis 2022; 54(07): 1843-1849
DOI: 10.1055/a-1639-0648

paper

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

Authors

Jianfeng Li∗

^aSchool of Chinese Materia Medica and Yunnan Key Laboratory of Southern Medicinal Utilization, Yunnan University of Traditional Chinese Medicine, 1076 Yuhua Road, Chenggong District, Kunming 650106, P. R. of China
Xiaoting Wang

^bYunnan Shureli Biopharmaceutical Corporation, Ltd., 285 Xinguang Alley, Wuhua District, Kunming, Yunnan, P. R. of China
Rong-Ping Zhang∗

^aSchool of Chinese Materia Medica and Yunnan Key Laboratory of Southern Medicinal Utilization, Yunnan University of Traditional Chinese Medicine, 1076 Yuhua Road, Chenggong District, Kunming 650106, P. R. of China
Lei Chen

^aSchool of Chinese Materia Medica and Yunnan Key Laboratory of Southern Medicinal Utilization, Yunnan University of Traditional Chinese Medicine, 1076 Yuhua Road, Chenggong District, Kunming 650106, P. R. of China

Abstract

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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

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References

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Supplementary Material

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