title: Total synthesis of serofendic acids A and B employing tin-free homoallyl-homoallyl radical rearrangement.
abstract: Total syntheses of serofendic acids A (1a) and B (1b) are described. The key strategic element of the approach involves the novel tin-free homoallyl-homoallyl radical rearrangement of 5 for the construction of bicyclo[2.2.2]octane ring system 4. In addition, the conversion of methyl atisirenoate 2 to serofendic acids A (1a) and B (1b) was achieved on the basis of the Michael reaction of sodium thiomethoxide.[reaction: see text]
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan. toyota@c.s.osakafu-u.ac.jp
authors.forename: Masahiro
authors.initials: M
authors.lastname: Toyota
authors.forename: Takeshi
authors.initials: T
authors.lastname: Asano
authors.forename: Masataka
authors.initials: M
authors.lastname: Ihara
mesh_terms: D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D018696:Neuroprotective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry
chemical_list: D004224:Diterpenes; D018696:Neuroprotective Agents; C452642:serofendic acid; D014001:Tin