title: Total syntheses of (+/-)-crinine, (+/-)-crinamine, and (+/-)-6a-epi-crinamine via the regioselective synthesis and Diels-Alder reaction of 3-aryl-5-bromo-2-pyrone.
abstract: We have devised a new unified synthetic protocol to (+/-)-crinine, (+/-)-crinamine, and (+/-)-6a- epi-crinamine from the Diels-Alder cycloadduct of 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone with TBS vinyl ether. The requisite 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone was prepared from the C3-selective Stille coupling reaction of 3,5-dibromo-2-pyrone. Also noted is that the vinyl bromide can be used as a handle for further derivatization.
authors.affiliation: Department of Chemistry, Hanyang University, Seoul, Korea 133-791.
authors.forename: Thanh Tam
authors.initials: TT
authors.lastname: Nguyen
authors.forename: Jayhyok
authors.initials: J
authors.lastname: Chang
authors.forename: Eun-Ju
authors.initials: EJ
authors.lastname: Jung
authors.forename: Cheon-Gyu
authors.initials: CG
authors.lastname: Cho
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis*; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D047151:Amaryllidaceae Alkaloids; D011753:Pyrones; C528221:crinine; C411129:crinamine