期刊
JOURNAL OF NATURAL PRODUCTS
卷 72, 期 2, 页码 243-247出版社
AMER CHEMICAL SOC
DOI: 10.1021/np8005452
关键词
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资金
- Department of Chemistry and College of Arts and Sciences at Indiana State University [12030168]
- Indiana State University Promising Scholar Award
- National Science Foundation [CHE0521075]
- NIDDK
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, beta 2-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.
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