title: Synthetic Studies on a Pachastrissamine Sulfur Analogue: Synthesis of a 4-epi-Sulfur Analogue.
abstract: A versatile synthetic procedure for a sulfur analogue of pachastrissamine (jaspine B), which involves the tandem thiolation-cyclization of a 1,4-ditosylate to construct a tetrahydrothiophene ring, was developed. Nucleophilic amino substitution of a tetrahydrothiophene-4-sulfonate with unexpected retention of the configuration afforded the sulfur analogue of 4-epi-pachastrissamine.
authors.affiliation: Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama.
authors.forename: Bo
authors.initials: B
authors.lastname: Liu
authors.forename: Kazuki
authors.initials: K
authors.lastname: Hashimoto
authors.forename: Hisanori
authors.initials: H
authors.lastname: Nambu
authors.forename: Tomoya
authors.initials: T
authors.lastname: Fujiwara
authors.forename: Takayuki
authors.initials: T
authors.lastname: Yakura
mesh_terms: D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry*
chemical_list: C468594:pachastrissamine; D013455:Sulfur; D013110:Sphingosine