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Biomimetic transformations of parthenolide
J Castañeda-Acosta1, N H Fischer, D Vargas
1Department of Chemistry, College of Basic Sciences, Louisiana State University, Baton Rouge 70803-1804.
Journal of Natural Products
|January 1, 1993
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.