Total Synthesis of Thuggacin B

Authors

  • Martin Bock,

    1. Institut für Organische Chemie und Biomolekulares Wirkstoffzentrum (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover (Germany), Fax: (+49) 511-762-3011
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  • Richard Dehn,

    1. Institut für Organische Chemie und Biomolekulares Wirkstoffzentrum (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover (Germany), Fax: (+49) 511-762-3011
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  • Andreas Kirschning Prof. Dr.

    1. Institut für Organische Chemie und Biomolekulares Wirkstoffzentrum (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover (Germany), Fax: (+49) 511-762-3011
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  • This research work was funded by the Stiftung Stipendien-Fonds des Verbandes der Chemischen Industrie (graduate scholarship for R.D.). We are indebted to H. Irschik (HZI, Braunschweig) and R. Jansen (HZI, Braunschweig) for authentic samples of the thuggacins. We thank E. Hofer for expert NMR support.

Abstract

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Final proof of the complete structures of thuggacins A–C was gained by a highly convergent and flexible total synthesis. Notable features include a substrate-controlled, titanium-mediated aldol reaction, a cross-metathesis approach for converting terminal alkenes into the corresponding vinyl iodides, and the cross-coupling of a complex vinyl iodide and terminal alkyne in the Sonogashira reaction.

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