title: Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives.
abstract: Tricyclic isotaxane and taxane derivatives have been synthesized by a very efficient cascade ring-closing dienyne metathesis (RCDEYM) reaction, which formed the A and B rings in one operation. When the alkyne is present at C13 (with no neighboring gem-dimethyl group), the RCEDYM reaction leads to 14,15-isotaxanes 16 a,b and 18 b with the gem-dimethyl group on the A ring. If the alkyne is at the C11 position (and thus flanked by a gem-dimethyl group), RCEDYM reaction only proceeds in the presence of a trisubstituted olefin at C13, which disfavors the competing diene ring-closing metathesis reaction, to give the tricyclic core of Taxol 44.
authors.affiliation: Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, DCSO, 91128, Palaiseau, France.
authors.forename: Cong
authors.initials: C
authors.lastname: Ma
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow, G12 8QQ, UK.
authors.forename: Aurélien
authors.initials: A
authors.lastname: Letort
authors.affiliation: Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, DCSO, 91128, Palaiseau, France.
authors.forename: Rémi
authors.initials: R
authors.lastname: Aouzal
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow, G12 8QQ, UK.
authors.forename: Antonia
authors.initials: A
authors.lastname: Wilkes
authors.affiliation: Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, DCSO, 91128, Palaiseau, France.
authors.forename: Gourhari
authors.initials: G
authors.lastname: Maiti
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow, G12 8QQ, UK.
authors.forename: Louis J
authors.initials: LJ
authors.lastname: Farrugia
authors.affiliation: Laboratoire de Chimie Moléculaire, CNRS UMR 9168, Ecole Polytechnique, LCM, 91128, Palaiseau, France.
authors.forename: Louis
authors.initials: L
authors.lastname: Ricard
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow, G12 8QQ, UK. joelle.prunet@glasgow.ac.uk.
authors.forename: Joëlle
authors.initials: J
authors.lastname: Prunet
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D003516:Cycloparaffins / Q000138:chemical synthesis; D007536:Isomerism; D015394:Molecular Structure; D043823:Taxoids / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000480:Alkynes; D001952:Bridged-Ring Compounds; D003516:Cycloparaffins; D043823:Taxoids; C080625:taxane
keywords: cyclooctenes; enyne; metathesis; synthesis design; taxanes