Total synthesis of four natural trans-stilbene O-glucosides

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-02-01 DOI:10.1016/j.tet.2024.134417

Haiping Qiu, Zongjun Tang, Wenjin Ma, Jiayao Yuan, Wenling Li

引用次数: 0

Abstract

The regioselective total synthesis of four natural stilbene O-glucosides was extensively investigated. The trans double bond of stilbene O-glucoside intermediates was constructed through the key Wittig reactions of O-glycosylated benzaldehydes with phosphorus ylides and subsequent cis/trans-isomerization reactions. The final global deprotection reactions successfully led to the production of the O-glucoside monomers of resveratrol, piceatannol, and oxyresveratrol. This work reports the first synthesis of a gentol O-glucoside.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.