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Assembly of the Entire Carbon Backbone of a Stereoisomer of the Antitumor Marine Natural Product Hemicalide |
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| Authors: | Dr Camille Lecourt Sabrina Dhambri Khalil Yamani Dr Guillaume Boissonnat Dr Simon Specklin Dr Etienne Fleury Karim Hammad Eric Auclair Serge Sablé Dr Antonio Grondin Dr Paola B Arimondo Dr François Sautel Dr Georges Massiot Dr Christophe Meyer Prof Dr Janine Cossy Dr Geoffroy Sorin Dr Marie-Isabelle Lannou Prof Dr Janick Ardisson |
| Institution: | 1. CNRS (UMR8638), Faculté de Pharmacie, Université Paris Descartes, 4 avenue de l'observatoire, 75270 Paris Cedex 06, France
Laboratory of Organic Chemistry, Chemistry, Biology, Innovation, ESPCI Paris, CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France;2. CNRS (UMR8638), Faculté de Pharmacie, Université Paris Descartes, 4 avenue de l'observatoire, 75270 Paris Cedex 06, France;3. Laboratory of Organic Chemistry, Chemistry, Biology, Innovation, ESPCI Paris, CNRS (UMR8231), PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France;4. Sanofi R&D, Centre de Recherche de Vitry-Alfortville, 13 quai Jules Guesde, 94403 Vitry-sur-Seine Cedex, France;5. Pharmacochimie de la Régulation Epigénétique du Cancer (ETac), CNRS–Pierre Fabre (USR3388), 3 avenue Hubert Curien, 31035 Toulouse Cedex 01, France |
| Abstract: | A strategy for the assembly of the entire carbon backbone of a stereoisomer of the antitumor marine natural product hemicalide has been investigated. The devised convergent approach relies on Horner–Wadsworth–Emmons and Julia–Kocienski olefination reactions for the construction of the C6=C7 and C34=C35 double bonds, respectively, an aldol reaction to create the C27−C28 bond, and a Suzuki–Miyaura cross-coupling as the endgame to form the C15−C16 bond. |
| Keywords: | hemicalide multistep synthesis natural products polyketides stereochemistry |