Biomimetic transformations of parthenolide.
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.
Castañeda-Acosta
J
J
Department of Chemistry, College of Basic Sciences, Louisiana State University, Baton Rouge 70803-1804.
Fischer
N H
NH
Vargas
D
D
D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane / Q000737:chemistry*; D013329:Structure-Activity Relationship
D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane; C577928:micheliolide; C002669:parthenolide