title: Synthetic studies on hemicalide: development of a convergent approach toward the C1-C25 fragment.
abstract: Synthetic studies on hemicalide, a recently isolated marine natural product displaying highly potent antiproliferative activity and a unique mode of action, have highlighted a reliable Horner-Wadsworth-Emmons olefination to create the C6-C7 alkene and a remarkable efficient Suzuki-Miyaura coupling to form the C15-C16 bond, resulting in the development of a convergent approach toward the C1-C25 fragment.
authors.affiliation: Faculté de Pharmacie, Université Paris Descartes , CNRS UMR 8638, 4 avenue de l'observatoire, 75270 Paris Cedex 06, France, CNRS-Pierre Fabre USR 3388 , Centre de Recherche & Développement Pierre Fabre, 3 avenue Hubert Curien, 31035 Toulouse Cedex 01, France, and Laboratoire de Chimie Organique, ESPCI ParisTech , CNRS UMR 7084, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Geoffroy
authors.initials: G
authors.lastname: Sorin
authors.forename: Etienne
authors.initials: E
authors.lastname: Fleury
authors.forename: Christine
authors.initials: C
authors.lastname: Tran
authors.forename: Elise
authors.initials: E
authors.lastname: Prost
authors.forename: Nicolas
authors.initials: N
authors.lastname: Molinier
authors.forename: François
authors.initials: F
authors.lastname: Sautel
authors.forename: Georges
authors.initials: G
authors.lastname: Massiot
authors.forename: Simon
authors.initials: S
authors.lastname: Specklin
authors.forename: Christophe
authors.initials: C
authors.lastname: Meyer
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
authors.forename: Marie-Isabelle
authors.initials: MI
authors.lastname: Lannou
authors.forename: Janick
authors.initials: J
authors.lastname: Ardisson
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000970:Antineoplastic Agents; D001688:Biological Products; D061065:Polyketides; C586602:hemicalide