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Synthesis 2019; 51(16): 3127-3141
DOI: 10.1055/s-0037-1610707
DOI: 10.1055/s-0037-1610707
paper
Synthesis of Bisflavanol-Type Natural Products and Their Analogues via Self-Coupling of C8-Methylol Catechin Derivatives
This work was supported by the National Natural Science Foundation of China (21672046 and 21372054), the Fundamental Research Funds for the Central Universities (HIT.NSRIF.201701), and the Foundation from Huancui District of Wehai City.Further Information
Publication History
Received: 13 January 2019
Accepted after revision: 25 March 2019
Publication Date:
24 April 2019 (online)
Abstract
A highly efficient and regioselective self-coupling of C8-methylol catechin derivatives is developed for the synthesis of dimeric flavanol analogues under metal-free and mild conditions. Its applicability is showcased by the efficient synthesis of bisflavanol-type natural products bis-8,8′-catechinylmethane, bis-8,8′-epicatechinylmethane, talienbisflavan A, and oolonghomobisflavan A. The novel self-coupling mechanism sheds new light on the classical Friedel–Crafts alkylation mechanism in acid-catalyzed catechin–formaldehyde condensation.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610707.
- Supporting Information
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