Total synthesis of alternariol

被引：147

作者：

Koch, K

Podlech, J

Pfeiffer, E

Metzler, M

机构：

[1] Univ Karlsruhe, Inst Organ Chem, D-76131 Karlsruhe, Germany

[2] Univ Karlsruhe, Inst Lebensmittelchem & Toxikol, D-76131 Karlsruhe, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 08期

关键词：

D O I：

10.1021/jo050075r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of alternariol, a toxic secondary metabolite of various Alternaria fungi, was achieved in seven steps starting with orcinol and 3,5-dimethoxybromobenzene. The longest linear sequence consists of six steps. Key reaction is a palladium-catalyzed Suzuki-type coupling of an orcinol-derived boronic acid with a brominated resorcylic aldehyde. The final demethylation furnished alternariol in 73% yield containing a smaller fraction of alternariol 9-methyl ether (similar to 20%).

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页码：3275 / 3276

页数：2

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