title: Exceedingly Efficient Synthesis of (±)-Grandifloracin and Acylated Analogues.
abstract: A highly efficient regio- and stereoselective total synthesis of (±)-grandifloracin via a tandem dearomative epoxidation/spontaneous Diels-Alder cyclodimerization from salicylic acid in only four steps is reported. The synthetic route allows for late-stage diversification of the core structure to give ready access to analogues of this promising agent against pancreatic cancer.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States.
authors.forename: Magnus
authors.initials: M
authors.lastname: Bergner
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States.
authors.forename: Douglas C
authors.initials: DC
authors.lastname: Duquette
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States.
authors.forename: Linda
authors.initials: L
authors.lastname: Chio
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States.
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: D000215:Acylation; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D061565:Cycloaddition Reaction; D019281:Dimerization; D015394:Molecular Structure; D010190:Pancreatic Neoplasms / Q000188:drug therapy*; D020156:Salicylic Acid / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D001952:Bridged-Ring Compounds; C560843:grandifloracin; D020156:Salicylic Acid