Shaun R Patel

Wabash College, کرافوردزویل، ایندیانا, Indiana, United States

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Publications (1)3.8 Total impact

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    ABSTRACT: In 2003, we reported the isolation, structure elucidation, and pharmacology of epiquinamide (1), a novel alkaloid isolated from an Ecuadoran poison frog, Epipedobates tricolor. Since then, several groups, including ours, have undertaken synthetic efforts to produce this compound, which appeared initially to be a novel, beta2-selective nicotinic acetylcholine receptor agonist. Based on prior chiral GC analysis of synthetic and natural samples, the absolute structure of this alkaloid was established as (1S,9aS)-1-acetamidoquinolizidine. We have synthesized the (1R*,9aS*)-isomer (epi-epiquinamide) using an iminium ion nitroaldol reaction as the key step. We have also synthesized ent-1 semisynthetically from (-)-lupinine. Synthetic epiquinamide is inactive at nicotinic receptors, in accord with recently published reports. We have determined that the activity initially reported is due to cross-contamination from co-occurring epibatidine in the isolated material.
    Journal of Natural Products 03/2009; 72(2):243-7. DOI:10.1021/np8005452 · 3.80 Impact Factor

Publication Stats

21 Citations
3.80 Total Impact Points

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  • 2009
    • Wabash College
      • Chemistry
      کرافوردزویل، ایندیانا, Indiana, United States