title: Formal synthesis of dictyostatin and synthesis of two dictyostatin analogues.
abstract: A formal convergent synthesis of dictyostatin from (R)-Roche ester is described. Synthetic highlights include a Ni-catalyzed Nozaki-Hiyama-Kishi coupling between an aldehyde and a Z vinyl iodide to assemble the two main fragments, a diastereoselective Myers alkylation, a stereoselective Evans aldolization, two asymmetric Duthaler crotyltitanations, and a stereoselective Pd-catalyzed Marshall allenylindium addition to install the stereogenic centers of dictyostatin. The synthesis of (9R)-epi-dictyostatin and a new ring-contracted dictyostatin isomer were also achieved.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI ParisTech, UMR CNRS 7084, 10, Rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Julien
authors.initials: J
authors.lastname: Gallon
authors.forename: Jorge
authors.initials: J
authors.lastname: Esteban
authors.forename: Samir
authors.initials: S
authors.lastname: Bouzbouz
authors.forename: Matthew
authors.initials: M
authors.lastname: Campbell
authors.forename: Sébastien
authors.initials: S
authors.lastname: Reymond
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; C470814:dictyostatin