title: Synthesis of β-methoxyacrylate natural products based on box-Pd(II)-catalyzed intermolecular methoxycarbonylation of alkynoles.
abstract: Bis(oxazoline)-palladium(II) catalyzed carbonylation of homopropargyl alcohols afforded acyclic methoxyacrylate 2 and 6-membered lactone 3a-k in good combined yield. In the case of propargyl alcohols, 5-membered lactones 3p, 3q, 16 were obtained in moderate yields. The one-pot synthesis of kawa lactones 3a, 3r, 3s and formal synthesis of dihydroxycystothiazole A and dihydroxycystothiazole C are presented. To elucidate the stereochemistry of (+)-annularin G and (-)-annularin H, the first asymmetric syntheses of these natural products were achieved.
authors.affiliation: Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Motodate
authors.forename: Takuya
authors.initials: T
authors.lastname: Kobayashi
authors.forename: Mikio
authors.initials: M
authors.lastname: Fujii
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Mochida
authors.forename: Taichi
authors.initials: T
authors.lastname: Kusakabe
authors.forename: Shigeki
authors.initials: S
authors.lastname: Katoh
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Akita
authors.forename: Keisuke
authors.initials: K
authors.lastname: Kato
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000179:Acrylates / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C555041:4-methoxy-5-(2-hydroxybutyl)-2,(5H)-furanone; C555042:4-methoxy-5-(2-oxobutyl)-2,(5H)-furanone; D000179:Acrylates; D001688:Biological Products; D007783:Lactones; D010165:Palladium; D015107:4-Butyrolactone