title: Synthetic Studies toward the C32-C46 Segment of Hemicalide. Assignment of the Relative Configuration of the C36-C42 Subunit.
abstract: The synthesis of five diastereomeric model compounds incorporating the C32-C46 segment of the antitumor marine natural product hemicalide has been achieved through a convergent approach relying on the 1,4-addition of an alkenyl boronate to an α,β-unsaturated δ-lactone followed by α-hydroxylation of an enolate and a Julia-Kocienski olefination. Comparison of the (1)H and (13)C NMR data of the model compounds with those of hemicalide enabled the assignment of the relative configuration of the C36-C42 subunit.
authors.affiliation: †Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), ESPCI ParisTech, CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Simon
authors.initials: S
authors.lastname: Specklin
authors.affiliation: †Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), ESPCI ParisTech, CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Boissonnat
authors.affiliation: ‡Faculté de Pharmacie, Université Paris Descartes, CNRS (UMR8638), 4 avenue de l'observatoire, 75270 Paris Cedex 06, France.
authors.forename: Camille
authors.initials: C
authors.lastname: Lecourt
authors.affiliation: ‡Faculté de Pharmacie, Université Paris Descartes, CNRS (UMR8638), 4 avenue de l'observatoire, 75270 Paris Cedex 06, France.
authors.forename: Geoffroy
authors.initials: G
authors.lastname: Sorin
authors.affiliation: ‡Faculté de Pharmacie, Université Paris Descartes, CNRS (UMR8638), 4 avenue de l'observatoire, 75270 Paris Cedex 06, France.
authors.forename: Marie-Isabelle
authors.initials: MI
authors.lastname: Lannou
authors.affiliation: ‡Faculté de Pharmacie, Université Paris Descartes, CNRS (UMR8638), 4 avenue de l'observatoire, 75270 Paris Cedex 06, France.
authors.forename: Janick
authors.initials: J
authors.lastname: Ardisson
authors.affiliation: §Pharmacochimie de la Régulation Epigénétique du Cancer (ETac), CNRS/Pierre Fabre (USR3388), Centre de Recherche et de Développement Pierre Fabre, 3 avenue Hubert Curien, 31035 Toulouse Cedex 01, France.
authors.forename: François
authors.initials: F
authors.lastname: Sautel
authors.affiliation: §Pharmacochimie de la Régulation Epigénétique du Cancer (ETac), CNRS/Pierre Fabre (USR3388), Centre de Recherche et de Développement Pierre Fabre, 3 avenue Hubert Curien, 31035 Toulouse Cedex 01, France.
authors.forename: Georges
authors.initials: G
authors.lastname: Massiot
authors.affiliation: †Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), ESPCI ParisTech, CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Meyer
authors.affiliation: †Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), ESPCI ParisTech, CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D001688:Biological Products; D061065:Polyketides; C586602:hemicalide