title: Biomimetic transformations of parthenolide.
abstract: An investigation of BF3-mediated rearrangements of parthenolide [1] provided micheliolide [5] as a major product. Minor reaction products included 10 (14)-dehydro-5 alpha-hydroxy-trans-guaianolide [2], 9,10-dehydro-5 alpha-hydroxy-trans-guaianolide [3], the xanthanolide 2-desoxy-6-epi-parthemollin [4], 1,2-dehydro-4 alpha-hydroxyguaianolide [6], 11,13-dehydrocompressanolide [7], and bicyclo[6.2.0]dec-10(14)-en-12,6-olide [8]. Their mechanisms of formation were interpreted as rearrangements involving carbocation intermediates.
authors.affiliation: Department of Chemistry, College of Basic Sciences, Louisiana State University, Baton Rouge 70803-1804.
authors.forename: J
authors.initials: J
authors.lastname: Castañeda-Acosta
authors.forename: N H
authors.initials: NH
authors.lastname: Fischer
authors.forename: D
authors.initials: D
authors.lastname: Vargas
mesh_terms: D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane; C577928:micheliolide; C002669:parthenolide