Jonathan Hempel
Last active: 3/25/2014

The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine akaloids lamellarin G trimethyl ether and ningalin B.

Gupton JT, Giglio BC, Eaton JE, Rieck EA, Smith KL, Keough MJ, Barelli PJ, Firich LT, Hempel JE, Smith TM, Kanters RP
Tetrahedron. 2009 65 (22): 4283-4292

PMID: 20161334 · PMCID: PMC2678759 · DOI:10.1016/j.tet.2009.03.085

Studies directed at the synthesis of lamellarin G trimethyl ether and ningalin B via vinylogous iminium salt derivatives are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 1,2,3,4-tetrasubstituted pyrrole from a vinylogous iminium salt or vinylogous iminium salt derivative. Subsequent transformations of these highly substituted pyrroles lead to efficient and regiocontrolled formal syntheses of the respective pyrrole containing natural products.

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