Total Synthesis of Auripyrones A and B and Determination of the Absolute Configuration of Auripyrone B

Authors

  • Ichiro Hayakawa Dr.,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan), Fax: (+81) 29-853-4313
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  • Takuma Takemura,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan), Fax: (+81) 29-853-4313
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  • Emi Fukasawa,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan), Fax: (+81) 29-853-4313
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  • Yuta Ebihara,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan), Fax: (+81) 29-853-4313
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  • Natsuki Sato,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan), Fax: (+81) 29-853-4313
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  • Takayasu Nakamura,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan), Fax: (+81) 29-853-4313
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  • Kiyotake Suenaga Dr.,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan), Fax: (+81) 29-853-4313
    2. Present address: Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku, Yokohama, Kanagawa 223-8522 (Japan)
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  • Hideo Kigoshi Prof. Dr.

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan), Fax: (+81) 29-853-4313
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  • This work was supported by Grants-in-Aid for Scientific Research (B), and Scientific Research on Priority Area “Creation of Biologically Functional Molecules” from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) (Japan). We thank the Kaneka Corporation for their gift of methyl D-(R)-β-hydroxyisobutanoate.

Abstract

original image

Mit Aldol zum Erfolg: Eine diastereoselektive Aldolreaktion mit 2,6-Diethyl-3,5-dimethyl-4-pyron war der Schlüsselschritt in der Totalsynthese der Auripyrone A und B. Die stereochemischen Verhältnisse und die absolute Konfiguration von Auripyron B wurden ebenfalls bestimmt.

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