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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∗
a   School 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
b   Yunnan Shureli Biopharmaceutical Corporation, Ltd., 285 Xinguang Alley, Wuhua District, Kunming, Yunnan, P. R. of China
,
Rong-Ping Zhang∗
a   School 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
a   School 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
› Author AffiliationsFunding for the Project of Supporting the Advanced Scholars in Yunnan­ Province (30271101200).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1639-0648.
  • Supporting Information


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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