title: The total syntheses of basiliolide C, epi-basiliolide C, and protecting-group-free total syntheses of transtaganolides C and D.
abstract: The total syntheses of basiliolide C and previously unreported epi-basiliolide C are achieved by an Ireland-Claisen/Diels-Alder cascade. The development of a palladium catalyzed cross-coupling of methoxy alkynyl zinc reagents allows for the protecting-group-free syntheses of transtaganolides C and D. Syntheses of transtaganolides C and D are accomplished in a single operation to generate three rings, two all-carbon quaternary centers, and four tertiary stereocenters from a monocyclic, achiral precursor.
authors.affiliation: 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: Jonny R
authors.initials: JR
authors.lastname: Gordon
authors.forename: Hosea M
authors.initials: HM
authors.lastname: Nelson
authors.forename: Scott C
authors.initials: SC
authors.lastname: Virgil
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: D037621:Artemisinins / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D037621:Artemisinins; D007202:Indicators and Reagents; D011753:Pyrones; C000597365:basiliolide C; C559846:transtaganolide C; C538700:transtaganolide D; D010165:Palladium; D015032:Zinc