title: Ring-construction/stereoselective functionalization cascade: total synthesis of pachastrissamine (jaspine B) through palladium-catalyzed bis-cyclization of propargyl chlorides and carbonates.
abstract: Palladium(0)-catalyzed cyclization of bromoallenes, propargyl chlorides, and carbonates bearing hydroxy and benzamide groups as internal nucleophiles stereoselectively provides functionalized tetrahydrofuran. Cyclization reactivity is dependent on the relative configuration of the benzamide and leaving groups, and on the nature of the leaving groups. This bis-cyclization was used as the key step in a short total synthesis of pachastrissamine, which is a biologically active marine natural product.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Shinsuke
authors.initials: S
authors.lastname: Inuki
authors.forename: Yuji
authors.initials: Y
authors.lastname: Yoshimitsu
authors.forename: Shinya
authors.initials: S
authors.lastname: Oishi
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Fujii
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Ohno
mesh_terms: D000480:Alkynes / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D003500:Cyclization; D010165:Palladium / Q000737:chemistry; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D002254:Carbonates; D002712:Chlorides; C468594:pachastrissamine; D010165:Palladium; D013110:Sphingosine