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(E)-13-(4-Amino-phen-yl)parthenolide.


ABSTRACT: The title compound, C21H25NO3 [systematic name: (3aS,9aR,10aR,10bS,E)-3-[(E)-4-(4-amino-benzyl-idene)-6,9a-dimethyl-3a,4,5,8,9,9a,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-b]furan-2(3H)-one] was obtained from the reaction of parthenolide [synonym: 4,5-ep-oxy-germacra-1(10),11(13)-dieno-12,6-lactone] with 4-iodo-aniline under Heck reaction conditions. It was identified as the E-isomer (conformation about the exocyclic methyl-idene C=C bond; the conformation about the C=C bond in the ten-membered ring is also E). The mol-ecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings with a 4-amino-phenyl group as a substituent. The ten-membered ring displays an approximate chair-chair conformation, while the lactone ring has an envelope conformation with th

SUBMITTER: Penthala NR 

PROVIDER: S-EPMC3884358 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature