期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 8, 页码 2599-2604出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902544
关键词
acylation; antibiotics; ravenic acid; tetramic acids; ylides
资金
- Deutsche Forschungsgemeinschaft [Scho 402/9-1, Sa 365/3-1]
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.
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