Enantiospecific Synthesis and Biological Investigations of a Nuphar Alkaloid: Proposed Structure of a Castoreum Component.
An enantiospecific synthesis of a Nuphar alkaloid was achieved in 9 steps fromN-Boc-(L)-proline. The alkaloid is a minor component of castoreum, the dried scent glands of the beaver. During the course of our study, the stereochemistry of three synthetic intermediates was verified by X-ray analysis, which contributes to resolving existing discrepancies among the literature reports regarding the synthesis of this particular compound. Based on our synthesis, we propose the structure of the natural product. Also, intrigued by castoreum's therapeutic effect, which was used in ancient Greece and Rome for gynecological and other purposes, biological screening was conducted. We found that the alkaloid has affinity for the oxytocin receptor.
Departments of Chemistry and Medicinal Chemistry, Institute for Therapeutics Discovery and Development, College of Pharmacy, University of Minnesota, 717 Delaware St. SE, Minneapolis MN 55414 U.S.A.
Hajime
H
Seki
Departments of Chemistry and Medicinal Chemistry, Institute for Therapeutics Discovery and Development, College of Pharmacy, University of Minnesota, 717 Delaware St. SE, Minneapolis MN 55414 U.S.A.
Gunda I
GI
Georg
alkaloid; castoreum; indolizidine; nuphar; oxytocin