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Light-Mediated Total Synthesis of 17-Deoxyprovidencin†

Authors

  • Dr. Nina Toelle,

    1. Universität Wien, Institute für Organische Chemie, Währinger Strasse 38, 1090 Wien (Austria)
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    • These authors contributed equally to this work.

  • Dr. Harald Weinstabl,

    1. Universität Wien, Institute für Organische Chemie, Währinger Strasse 38, 1090 Wien (Austria)
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    • These authors contributed equally to this work.

  • Dr. Tanja Gaich,

    1. Leibniz Universität Hannover, Institut für Organische Chemie, Schneiderberg 1B, 30167 Hannover (Germany)
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  • Prof. Dr. Johann Mulzer

    Corresponding author
    1. Universität Wien, Institute für Organische Chemie, Währinger Strasse 38, 1090 Wien (Austria)

    • Universität Wien, Institute für Organische Chemie, Währinger Strasse 38, 1090 Wien (Austria)===

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  • †

    N.T. is grateful to the Austrian FWF (Fonds zur Förderung der Wissenschaften) for a Lise Meitner fellowship (M1322). We also thank Hanspeter Kaehlig, Lothar Brecker, and Susanne Felsinger for the recording and help with the interpretation of NMR data and Vladimir Arion and Alexander Roller for crystal-structure analysis of 27 a.

Abstract

An asymmetric synthesis of the diterpenoid 17-deoxyprovidencin is described. Key steps include an aldol addition, a base-catalyzed Wipf-type furan formation, a Z-selective ring-closing metathesis for macrocyclization, a photochemical E/Z isomerization to a highly strained and conformationally restricted ring system, and the stereoselective formation of two epoxides on the ring.

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Article Information

DOI

10.1002/anie.201400617

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© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Keywords

  • furanocembranoids;
  • macrocycles;
  • metathesis;
  • photoisomerization;
  • total synthesis

Publication History

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  2. 2John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro, Michèle R. Prinsep, Marine natural products, Nat. Prod. Rep., 2016, 33, 3, 382CrossRef
  3. 3Samantha L. Kristufek, Guozhen Yang, Lauren A. Link, Brian J. Rohde, Megan L. Robertson, Karen L. Wooley, Synthesis, Characterization, and Cross-Linking Strategy of a Quercetin-Based Epoxidized Monomer as a Naturally-Derived Replacement for BPA in Epoxy Resins, ChemSusChem, 2016, 9, 16, 2135Wiley Online Library
  4. 4James W. Herndon, The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014, Coordination Chemistry Reviews, 2016, 317, 1CrossRef
  5. 5Jose F López-Acosta, Pablo Villa-Pérez, Cristina M Fernández-Díaz, Daniel de Luis Román, Ana R Díaz-Marrero, Mercedes Cueto, Germán Perdomo, Irene Cózar-Castellano, Protective effects of epoxypukalide on pancreatic β-cells and glucose metabolism in STZ-induced diabetic mice, Islets, 2015, 7, 2, e1078053CrossRef
  6. 6Nina Toelle, Harald Weinstabl, Tanja Gaich, Johann Mulzer, ChemInform Abstract: Light-Mediated Total Synthesis of 17-Deoxyprovidencin., ChemInform, 2014, 45, 36, noWiley Online Library