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The phytochemical investigation of the methylene chloride/methanol extract of the aerial parts of Artemisia herba-alba afforded two new natural sesquiterpene lactones 1β,9β-diacetoxyeudesm-3-en-5α,6β,11βH-12,6-olide (1) and 1β,9β-diacetoxyeudesm-4-en-6β,11βH-12,6-olide (2). The structures of the compounds were determined by comprehensive NMR studies, including DEPT, COSY, NOESY, HMQC, HMBC and HRMS.
Only two of the four possible facial approaches of cyclohexa-1,3-diene to the double bond in 2-methyl-5,6-benzo-2-azabicyclo[2.2.2]oct-7-en-3-one 7 are observed, giving exo,endo- and endo,endo-Diels-Alder cycloadducts 10a and 11a at atmospheric pressure (exo- and endo-defined here by reference to the benzo- and etheno-bridges, respectively). Hydride reduction of the carbonyl in 10a provides an indirect...
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