A Selective 3-Acylation of Tetramic Acids and the First Synthesis of Ravenic Acid

被引：29

作者：

Schlenk, Andrea ^{[1
]}

Diestel, Randi ^{[2
]}

Sasse, Florenz ^{[2
]}

Schobert, Rainer ^{[1
]}

机构：

[1] Univ Bayreuth, Organ Chem Lab, D-95440 Bayreuth, Germany

[2] Helmholtz Ctr Infect Res, Dept Biol Chem, D-38124 Braunschweig, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 08期

关键词：

acylation; antibiotics; ravenic acid; tetramic acids; ylides; STEREOSELECTIVE-SYNTHESIS; 3-ACYLTETRAMIC ACIDS; C-ACYLATION; DERIVATIVES; FACILE; CHEMISTRY; ANALOGS; ROUTE;

D O I：

10.1002/chem.200902544

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

3-Acyltetramic acids, including delicate 3-oligoenoyl derivatives, such as the Penicillium metabolite ravenic acid, were prepared in two high-yielding steps. Reaction of tetramic acids with the ylide Ph3PCCO afforded exclusively the corresponding 3-acylylidenetetramic acids. These were amenable to Wittig olefinations with aliphatic, aromatic, saturated and unsaturated aldehydes after deprotonation with KOtBu. Due to its simplicity, selectivity and tolerance of pH-sensitive groups this method is superior to the established acylation protocols by Jones and Yoshii. It is also applicable to the synthesis of 3-acyltetronic acids. The new 3-oligoenoyl tetramic acids exhibited structure-dependent antimicrobial and cytotoxic activity.

引用

页码：2599 / 2604

页数：6

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