title: Synthesis of demissidine by a ring fragmentation 1,3-dipolar cycloaddition approach.
abstract: A synthesis of the steroidal alkaloid demissidine from epiandrosterone is reported. A ring fragmentation reaction that efficiently ruptured the D-ring of a diazo ester derivative of epiandrosterone to provide an aldehyde tethered ynoate product was key to this sequence. Incorporation of the indolizidine framework was achieved by an azomethine ylide 1,3-dipolar cycloaddition.
authors.affiliation: The University of Vermont, 82 University Place, Burlington, Vermont 05405, United States.
authors.forename: Zhe
authors.initials: Z
authors.lastname: Zhang
authors.forename: Geoffrey M
authors.initials: GM
authors.lastname: Giampa
authors.forename: Cristian
authors.initials: C
authors.lastname: Draghici
authors.forename: Qiufeng
authors.initials: Q
authors.lastname: Huang
authors.forename: Matthias
authors.initials: M
authors.lastname: Brewer
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D054836:Indolizidines / Q000737:chemistry*; D012991:Solanaceous Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D054836:Indolizidines; D012991:Solanaceous Alkaloids; C015108:demissidine