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Enantioselective Total Synthesis of (+)-Dihydro-β-erythroidine.
J Am Chem Soc
June 2019
Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences , University of Copenhagen , Universitetsparken 2, 2100 Copenhagen , Denmark.
Erythrina alkaloids represent a rich source of complex polycyclic, bioactive natural products. In addition to their sedative and hypotensive effect, their curare-like activity and structural framework have made them attractive targets for synthetic and medicinal chemists. (+)-Dihydro-β-erythroidine (DHβE), the most potent nicotine acetylcholine receptor antagonist (nAChR) of the Erythrina family, is synthesized for the first time in 13 steps from commercially available material.
View Article and Find Full Text PDFTotal synthesis of natural products using hypervalent iodine reagents.
Front Chem
January 2015
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Département de Chimie, Université du Québec à Montréal Montréal, QC, Canada.
We present a review of natural product syntheses accomplished in our laboratory during the last 5 years. Each synthetic route features a phenol dearomatization promoted by an environmentally benign hypervalent iodine reagent. The dearomatizations demonstrate the "aromatic ring umpolung" concept, and involve stereoselective remodeling of the inert unsaturations of a phenol into a highly functionalized key intermediate that may contain a quaternary carbon center and a prochiral dienone system.
View Article and Find Full Text PDFIsostrychnopentamine, an indolomonoterpenic alkaloid from Strychnos usambarensis, induces cell cycle arrest and apoptosis in human colon cancer cells.
J Pharmacol Exp Ther
March 2003
Natural and Synthetic Drug Research Center, Laboratory of Pharmacognosy and Structural Chemistry, University of Liège, Liège, Belgium.
Isostrychnopentamine (ISP) is an indolomonoterpenic alkaloid that is present in the leaves of Strychnos usambarensis, a well known African shrub or little tree. The roots contain quaternary alkaloids, which are used to make a curare-like arrow poison. However, tertiary alkaloids isolated from the same plant possess cytotoxic activities against mammalian cells and protozoa.
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