Total Synthesis of Neoaltenuene

被引：24
|
作者：
Altemoeller, Martina [1 ]
Podlech, Joachim [1 ]
机构：
[1] Univ Karlsruhe TH, KIT, Inst Organ Chem, D-76131 Karlsruhe, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 14期
关键词：
Cross-coupling; Palladium; Total synthesis; Toxins; ALTERNARIOL METHYL-ETHER; AZA-CLAISEN REARRANGEMENT; ATOM-TRANSFER CYCLIZATION; ACID; METABOLITES; MYCOTOXINS; ALTENUENE; DERIVATIVES; CATALYSTS; FUNGUS;
D O I：
10.1002/ejoc.200900125
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of neoaltenuene, a toxin produced by alternaria fungi, has been achieved for the first time in 14 steps in a yield of 10% starting from quinic acid and phloroglucinic acid, the longest linear sequence consisting of 10 steps. The key reaction was a palladium-catalyzed Suzuki-type coupling of an arene boronate with an iodinated cyclohexene. 4a-epi-Neoaltenuene, a non-natural isomer has been synthesized similarly. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码：2275 / 2282
页数：8
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