title: Assignment and stereocontrol of hibarimicin atropoisomers.
abstract: A stereochemical feature of the hibarimicins is a central biaryl (HMP-Y6) or aryl-quinone (hibarimicinone) incorporated as a single atropodiastereomer. Herein, a chiral resolution and deracemization process to access optically enriched biaryls aR-3 and aS-3 is described. From these atropoenantiomers the BCD-EFG ring system of HMP-Y6 is constructed [(+)-aR-7]. Comparison of CD spectra of aR-7 to HMP-Y6 leads to the assignment of HMP-Y6 and hibarimicin B atropoisomers as aR and aS, respectively.
authors.affiliation: Department of Chemistry, Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, USA.
authors.forename: Ian M
authors.initials: IM
authors.lastname: Romaine
authors.forename: Jonathan E
authors.initials: JE
authors.lastname: Hempel
authors.forename: Ganesh
authors.initials: G
authors.lastname: Shanmugam
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Hori
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Igarashi
authors.forename: Prasad L
authors.initials: PL
authors.lastname: Polavarapu
authors.forename: Gary A
authors.initials: GA
authors.lastname: Sulikowski
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D009279:Naphthacenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D009279:Naphthacenes; C456032:hibarimicin B