Jonathan Hempel
Last active: 3/25/2014

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

Gupton JT, Banner EJ, Sartin MD, Coppock MB, Hempel JE, Kharlamova A, Fisher DC, Giglio BC, Smith KL, Keough MJ, Smith TM, Kanters RP, Dominey RN, Sikorski JA
Tetrahedron. 2008 64 (22): 5246-5253

PMID: 18709182 · PMCID: PMC2516947 · DOI:10.1016/j.tet.2008.03.038

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.

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