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

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

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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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