title: Concise entry to both enantiomers of 8-oxabicyclo[3.2.1]oct-3-en-2-one based on novel oxidative etherification: formal synthesis of (+)-sundiversifolide.
abstract: Both enantiomers of 8-oxabicyclo[3.2.1]oct-3-en-2-one (6) have been synthesized from 4-hydroxycyclohept-2-enone (3) on the basis of a novel oxidative cyclo-etherification using PhI(OH)OTs (Koser's reagent). (-)-(1S,5R)-8-Oxabicyclo[3.2.1]oct-3-en-2-one [(-)-6, 95% ee] was expeditiously transformed to (+)-sundiversifolide (1).
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.
authors.forename: Muneo
authors.initials: M
authors.lastname: Kawasumi
authors.forename: Naoki
authors.initials: N
authors.lastname: Kanoh
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Iwabuchi
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D006368:Helianthus / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014966:Xanthenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C561514:8-oxabicyclo(3.2.1)oct-3-en-2-one; D019086:Bridged Bicyclo Compounds, Heterocyclic; D014966:Xanthenes; C433844:sundiversifolide