(E)-13-(2-Bromo-phen-yl)micheliolide.
The title compound, C21H23BrO3 [systematic name: (3E,3aS,6Z,9R,9aS,9bS)-3-(2-bromo-benzyl-idene)-9-hy-droxy-6,9-dimethyl-3,3a,4,5,7,8,9,9a-octa-hydro-azuleno[4,5-b]furan-2(9bH)-one] was prepared by the reaction of 1-bromo-2-iodo-benzene with micheliolide [systematic name: (3aS,R,9aS,9bS,Z)-9-hy-droxy-6,9-dimethyl-3-methyl-ene-3,3a,4,5,7,8,9,9a-octa-hydro-azuleno[4,5-b]furan-2(9bH)-one] under Heck reaction conditions. The title compound exhibits intra-molecular O-H⋯O hydrogen bonding between the hy-droxy group and the lactone ring O atom, forming a ring of graph-set motif S(6). The 2-bromo-phenyl group is trans to the lactone ring, indicating that this is the E isomer (geometry of the exocyclic C=C bond). The dihedral angle between the benzene ring of the 2-bromo-phenyl moiety and the mean plane of the lactone ring is 51.68 (7)°.
Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.
Narsimha Reddy
NR
Penthala
Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.
Shobanbabu
S
Bommagani
Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.
Venumadhav
V
Janganati
Department of Chemistry, University of Kentucky, Lexington, KY 40506, USA.
Sean
S
Parkin
Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.
Peter A
PA
Crooks