title: Towards the Synthesis of Dihydrooxepino[4,3-b]pyrrole-Containing Natural Products via Cope Rearrangement of Vinyl Pyrrole Epoxides.
abstract: An approach to the dihydrooxepino[4,3-b]pyrrole core of diketopiperazine natural products which utilizes a vinyl pyrrole epoxide Cope rearrangement was investigated. It was found that an ester substituent on the epoxide was essential for the [3,3]-rearrangement to occur. Density functional calculations with M06-2X provided explanations for the effects of the pyrrole and ester groups on these rearrangements.
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne , Melbourne, Victoria 3010, Australia.
authors.forename: Alex
authors.initials: A
authors.lastname: Cameron
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne , Melbourne, Victoria 3010, Australia.
authors.forename: Brendan
authors.initials: B
authors.lastname: Fisher
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne , Melbourne, Victoria 3010, Australia.
authors.forename: Nicholas
authors.initials: N
authors.lastname: Fisk
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne , Melbourne, Victoria 3010, Australia.
authors.forename: Jessica
authors.initials: J
authors.lastname: Hummel
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne , Melbourne, Victoria 3010, Australia.
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: White
authors.affiliation: School of Chemistry & Molecular Biosciences, The University of Queensland , Brisbane, QLD 4072, Australia.
authors.forename: Elizabeth H
authors.initials: EH
authors.lastname: Krenske
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne , Melbourne, Victoria 3010, Australia.
authors.forename: Mark A
authors.initials: MA
authors.lastname: Rizzacasa
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D054659:Diketopiperazines / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry / Q000302:isolation & purification; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D001688:Biological Products; D054659:Diketopiperazines; D004852:Epoxy Compounds; D004952:Esters; D010879:Piperazines; D011758:Pyrroles; C067458:emestrin; C002500:aranotin