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Total Synthesis and Structural Reassignment of (+)-Dictyosphaeric Acid A: A Tandem Intramolecular Michael Addition/Alkene Migration Approach

Authors


  • We thank the BBSRC for studentship funding (A.R.B.), GlaxoSmithKline for CASE support, and the University of York for post-doctoral funding (G.D.M.). We are also grateful to Dr. A. C. Whitwood and R. Thatcher (University of York) for X-ray crystallography studies and to Dr. T. Dransfield (University of York) for invaluable assistance with mass spectrometry. We would also like to thank Prof. C. M. Ireland (University of Utah) for providing us with copies of 1H and 13C NMR spectra for compounds 1 and 2, and for helpful discussions. We also thank Dr. C. W. Barfoot for carrying out relevant model studies (to be reported in a full paper) and Archimica for a kind gift of T3P.

Abstract

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Auf die Probe gestellt: Die Totalsynthese der Titelverbindung umfasst als Schlüsselschritte eine Z-selektive Ringschlussmetathese und eine E-selektive intramolekulare Tandemsequenz aus Michael-Addition und Alkenwanderung. Anhand der NMR-Daten des Produkts konnte die stereochemische Konfiguration neu zugeordnet werden.

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