title: Total synthesis of (±)-clavilactones A, B, and proposed D through iron-catalyzed carbonylation-peroxidation of olefin.
abstract: Biologically significant clavilactones A, B, and the previously proposed D have been synthesized through iron-catalyzed carbonylation-peroxidation of a 1,5-diene. Three steps from aldehydes, alkenes, and tert-butylhydroperoxide build up α,β-epoxy-γ-butyrolactone skeleton as a key building block for synthesis of clavilactone family and its derivatives. Based on our results, the structure of the proposed clavilactone D is not correct and requires revision.
authors.affiliation: Department of Chemistry, Renmin University of China, Beijing 100872 (China) http://chem.ruc.edu.cn/ligroup/index.html.
authors.forename: Leiyang
authors.initials: L
authors.lastname: Lv
authors.forename: Baojian
authors.initials: B
authors.lastname: Shen
authors.forename: Zhiping
authors.initials: Z
authors.lastname: Li
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D007501:Iron / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001688:Biological Products; D007783:Lactones; C412054:clavilactone D; D007501:Iron
keywords: carbonylation-peroxidation; clavilactone; epoxides; iron catalysis; natural product synthesis