title: Formation of tetrahydrofurans via a 5-endo-tet cyclization of aziridines--synthesis of (-)-pachastrissamine.
abstract: The formation of tetrahydrofurans from 2-hydroxyalkyl-oxirane or aziridine is reported. The 5-endo-tet cyclization/ring opening of aziridine proceeded smoothly to give tetrahydrofurans (THFs) under mild conditions. In contrast, the corresponding process of oxirane was unsuccessful and a sequence of SN2 substitution/cyclization was required to form THFs. The application of the process to prepare ent-(-)-pachastrissamine is described.
authors.affiliation: Department of Chemistry, National Central University, 300 Jhong-Da Road, Jhong-Li, Taoyuan, Taiwan.
authors.forename: Chen-Wei
authors.initials: CW
authors.lastname: Lin
authors.forename: Sin-Wei
authors.initials: SW
authors.lastname: Liu
authors.forename: Duen-Ren
authors.initials: DR
authors.lastname: Hou
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D003500:Cyclization; D005027:Ethylene Oxide / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D001688:Biological Products; D005663:Furans; C468594:pachastrissamine; D005027:Ethylene Oxide; D013110:Sphingosine