title: Highly demanding cross-metathesis in the synthesis of the C16-C30 fragment of dolabelide C.
abstract: A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.
authors.affiliation: Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, DCSO, F-91128 Palaiseau, France.
authors.forename: Marie-Gabrielle
authors.initials: MG
authors.lastname: Braun
authors.forename: Aurélie
authors.initials: A
authors.lastname: Vincent
authors.forename: Mehdi
authors.initials: M
authors.lastname: Boumediene
authors.forename: Joëlle
authors.initials: J
authors.lastname: Prunet
mesh_terms: D007536:Isomerism; D018942:Macrolides / Q000138:chemical synthesis*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry
chemical_list: D018942:Macrolides; D020005:Propanols; C524147:dolabelide C; C006463:allyl alcohol