The Application of Vinylogous Iminium Salt Derivatives and Microwave Accelerated Vilsmeier-Haack Reactions to Efficient Relay Syntheses of the Polycitone and Storniamide Natural Products.

Tetrahedron
John T GuptonJames A Sikorski

Abstract

Studies directed at the synthesis of polycitone and storniamide natural products via vinylogous iminium salts and microwave accelerated Vilsmeier-Haack formylations are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 2,3,4-trisubstituted pyrrole from a vinamidinium salt or vinamidinium salt derivative followed by formylation at the 5-position of the pyrrole. Subsequent transformations of the selectively formylated pyrroles lead to efficient and regiocontrolled relay syntheses of the respective pyrrole containing natural products.

References

Jul 24, 2003·Chemical Society Reviews·Ayyappanpillai Ajayaghosh
Jul 30, 2004·Current Medicinal Chemistry. Anti-cancer Agents·Christian Bailly

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Citations

Oct 12, 2010·Natural Product Reports·Ian S YoungAlison Thompson
Jan 24, 2014·Journal of Medicinal Chemistry·Cassandra L FlemingFrederick M Pfeffer
Dec 24, 2010·Organic Letters·Qingjiang LiYanxing Jia

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