title: Collaborative Total Synthesis: Routes to (±)-Hippolachnin A Enabled by Quadricyclane Cycloaddition and Late-Stage C-H Oxidation.
abstract: Described herein are synthetic efforts toward the synthesis of hippolachnin A. Two independently devised routes from the Brown and Wood groups allowed for the synthesis of hippolachnin A from the unusual starting material, quadricyclane, by harnessing the power of late-stage C-H oxidation. Collaborative union of the best features of the two routes allowed for preparation of the molecule with improved efficiency.
authors: Department of Chemistry and Biochemistry, Baylor University , One Bear Place 97348, Waco, Texas 76798, United States.
authors: Monica E
authors: ME
authors: McCallum
authors: Department of Chemistry, Indiana University , 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States.
authors: Christopher M
authors: CM
authors: Rasik
authors: Department of Chemistry and Biochemistry, Baylor University , One Bear Place 97348, Waco, Texas 76798, United States.
authors: John L
authors: JL
authors: Wood
authors: Department of Chemistry, Indiana University , 800 East Kirkwood Avenue, Bloomington, Indiana 47405, United States.
authors: M Kevin
authors: MK
authors: Brown
mesh_terms: D001952:Bridged-Ring Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D061565:Cycloaddition Reaction; D006859:Hydrogen / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001952:Bridged-Ring Compounds; D061065:Polyketides; C585986:hippolachnin A; D002244:Carbon; D006859:Hydrogen; C513530:quadricyclane