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).
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.
