title: Total synthesis and stereochemical assignment of (±)-sorbiterrin A.
abstract: A concise, biomimetic approach to sorbiterrin A has been developed employing consecutive Michael additions of a 4-hydroxypyrone to a sorbicillinol derivative and silver nanoparticle-mediated bridged aldol/dehydration to construct the [3.3.1] ring system. The relative stereochemistry of sorbiterrin A was unambiguously confirmed by X-ray crystallographic analysis.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University , Boston, Massachusetts 02215, United States.
authors.forename: Chao
authors.initials: C
authors.lastname: Qi
authors.forename: Tian
authors.initials: T
authors.lastname: Qin
authors.forename: Daisuke
authors.initials: D
authors.lastname: Suzuki
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D060326:Chemistry Techniques, Synthetic; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003512:Cyclohexanones; D011084:Polycyclic Aromatic Hydrocarbons; C453419:sorbicillinol; C000592850:sorbiterrin A