Castañeda-Acosta J, Fischer N H, Vargas D
Department of Chemistry, College of Basic Sciences, Louisiana State University, Baton Rouge 70803-1804.
J Nat Prod. 1993 Jan;56(1):90-8. doi: 10.1021/np50091a013.
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.
对BF₃介导的小白菊内酯[1]重排反应的研究表明，米氏内酯[5]是主要产物。次要反应产物包括10(14)-脱氢-5α-羟基反式愈创木烷内酯[2]、9,10-脱氢-5α-羟基反式愈创木烷内酯[3]、黄原酸内酯2-脱氧-6-表-小白菊内酯[4]、1,2-脱氢-4α-羟基愈创木烷内酯[6]、11,13-脱氢压缩香醇内酯[7]和双环[6.2.0]癸-10(14)-烯-12,6-内酯[8]。它们的形成机制被解释为涉及碳正离子中间体的重排反应。
