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