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A selective 3-acylation of tetramic acids and the first synthesis of ravenic acid.
Schlenk, Andrea Diestel, Randi Sasse, Florenz Schobert, Rainer
Schlenk, Andrea
Diestel, Randi
Sasse, Florenz
Schobert, Rainer
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2010-02-22
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Abstract
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 Ph(3)PCCO 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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A selective 3-acylation of tetramic acids and the first synthesis of ravenic acid. 2010, 16 (8):2599-604 Chemistry
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Article
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en
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1521-3765