title: Biomimetic synthesis: discovery of xanthanolide dimers.
abstract: Starting from xanthatin, the biomimetic synthesis of 4β,5β-epoxyxanthatin-1α,4α-endoperoxide, a novel monomeric xanthanolide, has been achieved. Moreover, four unprecedented xanthanolide dimers were synthesized by three different dimerizations of xanthatin, either in a head-to-head or head-to-tail fashion. Notably, these dimeric compounds were firstly identified as artifacts in the laboratory, and two of them, mogolides A and B, proved to be natural products present in the Xanthium mogolium Kitag plant.
authors.affiliation: The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine and Collaborative Innovation Center for Biotherapy, Tsinghua University, Beijing 100084 (China).
authors.forename: Hai
authors.initials: H
authors.lastname: Shang
authors.forename: Junhua
authors.initials: J
authors.lastname: Liu
authors.forename: Ruiyang
authors.initials: R
authors.lastname: Bao
authors.forename: Yu
authors.initials: Y
authors.lastname: Cao
authors.forename: Kun
authors.initials: K
authors.lastname: Zhao
authors.forename: Chengqian
authors.initials: C
authors.lastname: Xiao
authors.forename: Bing
authors.initials: B
authors.lastname: Zhou
authors.forename: Lihong
authors.initials: L
authors.lastname: Hu
authors.forename: Yefeng
authors.initials: Y
authors.lastname: Tang
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D019281:Dimerization; D005663:Furans / Q000737:chemistry*; D007536:Isomerism; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010545:Peroxides / Q000138:chemical synthesis* / Q000737:chemistry; D031210:Xanthium / Q000737:chemistry / Q000378:metabolism
chemical_list: C000600613:4beta,5beta-epoxyxanthatin-1alpha,4alpha-endoperoxide; D001688:Biological Products; D005663:Furans; D007783:Lactones; D010545:Peroxides; C022186:xanthatin
keywords: biomimetic synthesis; cycloaddition; dimerization; natural products; photochemistry