title: Synthesis of a potent antimalarial amphilectene.
abstract: 7-Isocyano-11(20),14-epiamphilectadiene, the most potent of antimalarial amphilectenes, is synthesized in seven steps from readily available materials. The synthesis is enabled by a new dendrimeric triene (Danishefsky [3]-dendralene) and a new method for stereo- and chemoselective isocyanation. This chemistry provides a useful entry into an underexplored yet promising family of antimalarial terpenoids.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Sergey V
authors.initials: SV
authors.lastname: Pronin
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Shenvi
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology; D004224:Diterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D005347:Fibroblasts / Q000187:drug effects*; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000187:drug effects*
chemical_list: C581111:7-isocyano-11(20),14-epiamphilectadiene; D000962:Antimalarials; D004224:Diterpenes