title: Pentafulvene for the synthesis of complex natural products: total syntheses of (±)-pallambins A and B.
abstract: The first total syntheses of pallambins A and B are enabled by the use of pentafulvene in an unprecedented Diels-Alder reaction. After elaboration of the adduct through chemoselective cyclopropanation, strategic CH insertion affords the dense tetracyclic core of the natural products. 1,3-Dipolar cycloaddition and palladium(II)-catalyzed alkoxycarbonylation were leveraged for the construction of the hexacyclic scaffold en route to both natural products.
authors.affiliation: Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich (Switzerland) http://www.carreira.ethz.ch.
authors.forename: Christian
authors.initials: C
authors.lastname: Ebner
authors.affiliation: Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich (Switzerland) http://www.carreira.ethz.ch. carreira@org.chem.ethz.ch.
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D003517:Cyclopentanes / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis*
chemical_list: D001688:Biological Products; D003517:Cyclopentanes; D004224:Diterpenes; C572042:pallambin A; C572043:pallambin B; C017332:fulvene
keywords: CH insertion; cycloaddition; natural products; small-ring systems; total synthesis