Biomimetic synthesis of resorcylate natural products utilizing late stage aromatization:: Concise total syntheses of the marine antifungal agents 15G256ι and 15G256β

被引：74

作者：

Navarro, Ismael ^{[1
]}

Basset, Jean-Francois ^{[1
]}

Hebbe, Severine ^{[1
]}

Major, Sarah M. ^{[1
]}

Werner, Thomas ^{[1
]}

Howsham, Catherine ^{[1
]}

Brackow, Jan ^{[1
]}

Barrett, Anthony G. M. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 31期

关键词：

D O I：

10.1021/ja803445u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diketo-1,3-dioxin-2-ones underwent retro-Diels-Alder reaction on heating in toluene at 110 degrees C to generate alpha,gamma,epsilon-triketo-ketenes. These were trapped with alcohols to provide 2,4,6-triketocarboxylates, which were smoothly aromatized by sequential reaction with potassium carbonate and methanolic hydrogen chloride to give resorcylate esters. The reaction was applied in the total synthesis of the marine antifungal agents 15G256 beta (1), 15G256 iota (2), and 15G256 pi (3) and the mycotoxin S-(-)-zearalenone (4).

引用

页码：10293 / 10298

页数：6

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