Synthesis of stagonosporyne G from (−)-D-quinic acid

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-01-21 DOI:10.1016/j.tet.2025.134488

Kentaro Koyama, Hironori Okamura, Hirosato Takikawa

引用次数: 0

Abstract

Stagonosporyne G, a highly oxygenated cyclohexanoid isolated from the wheat pathogen Parastagonospora nodorum SN15, shows herbicidal activity against Arabidopsos thaliana and may contribute to the virulence of P. nodorum SN15 against wheat species. Herein, we report the first synthesis of stagonosporyne G from commercially available D-(−)-quinic acid via diastereoselective 1,4-addition of alkynylaluminum species, Rubottom oxidation, and Evans reduction of α-hydroxyenone as the key steps. The absolute configuration of the natural stagonosporyne G was confirmed by comparing the optical rotations of synthetic and natural compounds.

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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.