A New Secondary Metabolite from Alternaria Alternata: Structure Elucidation and Total Synthesis of Altenuic Acid IV

被引：7

作者：

Kohler, Dominik ^{[1
]}

Podlech, Joachim ^{[1
]}

机构：

[1] KIT, Inst Organ Chem, Fritz Haber Weg 6, D-76131 Karlsruhe, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 08期

关键词：

Mycotoxins; Fungal metabolites; Cross-coupling; Total synthesis; Natural products; ENDOPHYTIC FUNGUS; MYCOTOXINS ALTERNARIOL; METHYL-ETHER; BIOSYNTHESIS; DISCOVERY; ESTERS; NMR;

D O I：

10.1002/ejoc.201801801

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A putative intermediate in the biosynthesis of altenuic acids I-III was isolated from Alternaria alternata in the 1950ies and a sample survived over the decades. This resorcylic lactone named altenuic acid IV is a composite of a resorcylic and a muconic acid. Its structure was confirmed by NMR spectroscopy and by total synthesis. Altenuic acid IV was here obtained starting with 2-bromo-4,6-dimethoxybenzene and 4-methylbenzene-1,2-diol with a total yield of 20 %. The synthesis was achieved in ten steps where the longest sequence consists of seven steps. Key steps were an oxidative ring opening of a bromocresol furnishing a bromomuconate and its Suzuki coupling with a resorcylate-derived boronate.

引用

页码：1748 / 1753

页数：6

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