title: Concise entry to chiral 5-(4-hydroxybutyl)-2(5H)-furanone via HTIB-mediated novel oxidative fragmentation: formal total synthesis of (+)-dubiusamine A.
abstract: The concise synthesis of 5-(4-hydroxybutyl)-2(5H)furanone has been accomplished from 9-oxabicyclo[4.2.1]non-7-en-1-ol on the basis of HTIB [PhI(OH)OTs, a.k.a. Koser's reagent]-mediated novel oxidative fragmentation. Chiral (-)-(R)-5-(4-hydroxy-butyl)-2(5H)-furanone (>99% ee) was used for the formal total synthesis of (+)-dubiusamine A (1).
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578.
authors.forename: Muneo
authors.initials: M
authors.lastname: Kawasumi
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Iwabuchi
mesh_terms: D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D028223:Pinus / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005663:Furans; C583257:dubiusamine A