Enantioselective Total Syntheses of Three Cladiellins (Eunicellins): A General Approach to the Entire Family of Natural Products†
Corresponding Author
Prof. Dr. J. Stephen Clark
WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867
WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867Search for more papers by this authorRaphaëlle Berger
WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867
Search for more papers by this authorDr. Stewart T. Hayes
School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (United Kingdom)
Search for more papers by this authorDr. Lynne H. Thomas
WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867
Search for more papers by this authorDr. Angus J. Morrison
MSD, Newhouse, Lanarkshire, ML1 5SH (United Kingdom)
Search for more papers by this authorDr. Luca Gobbi
Discovery Chemistry (PRCB), F. Hoffmann-La Roche Ltd, Pharmaceuticals Division, 4070 Basel (Switzerland)
Search for more papers by this authorCorresponding Author
Prof. Dr. J. Stephen Clark
WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867
WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867Search for more papers by this authorRaphaëlle Berger
WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867
Search for more papers by this authorDr. Stewart T. Hayes
School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (United Kingdom)
Search for more papers by this authorDr. Lynne H. Thomas
WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ (United Kingdom), Fax: (+44) 141-330-6867
Search for more papers by this authorDr. Angus J. Morrison
MSD, Newhouse, Lanarkshire, ML1 5SH (United Kingdom)
Search for more papers by this authorDr. Luca Gobbi
Discovery Chemistry (PRCB), F. Hoffmann-La Roche Ltd, Pharmaceuticals Division, 4070 Basel (Switzerland)
Search for more papers by this authorWe thank the EPSRC, M.S.D. and F. Hoffmann-La Roche Ltd for financial support.
Graphical Abstract
Durch stereoselektive Umlagerung eines freien oder metallgebundenen Oxonium-Ylids, das durch rhodiumkatalysierte intramolekulare Cyclisierung des Diazoketons 1 erzeugt wurde, entstand der E-konfigurierte, O-verbrückte, bicyclische Ether (E)-2, der effizient in (−)-Cladiella-6,11-dien-3-ol überführt wurde. TBS=tert-Butyldimethylsilyl.
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- 17Crystal data for cladiell-11-ene-3,6,7-triol: C20H34O4, Mr=338.47, crystal dimensions 0.30×0.1×0.05 mm3, orthorhombic, space group P212121, a=6.9388(6), b=8.1850(10), c=33.548(3) Å, α=β=γ=90°, V=1905.3(3) Å3, Z=4, ρcalcd=1.18 Mg m−3, μ(MoKα)=0.08 mm−1, T=100(2) K.; 13 485 reflections collected of which 4356 were independent, 2θmax=55°. Structure solved by direct methods (SHELXS-97) and refined by full-matrix least squares against F2 (SHELXL-97), R1=0.074, wR2=0.096, 225 parameters. CCDC 787739 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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