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Total Synthesis of (±)-γ-Rubromycin on the Basis of Two Aromatic Pummerer-Type Reactions

Authors

  • Shuji Akai Prof. Dr.,

    1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-8229
    2. Current Address: School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan
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  • Keisuke Kakiguchi Dr.,

    1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-8229
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  • Yuka Nakamura,

    1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-8229
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  • Ikumi Kuriwaki,

    1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-8229
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  • Toshifumi Dohi Dr.,

    1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-8229
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  • Shusaku Harada,

    1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-8229
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  • Ozora Kubo,

    1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-8229
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  • Nobuyoshi Morita Dr.,

    1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-8229
    2. Current Address: Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan
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  • Yasuyuki Kita Prof. Dr.

    1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan, Fax: (+81) 6-6879-8229
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  • This research was supported by Grants-in-Aid for Scientific Research (S and A) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We thank Dr. Axel Zeeck of the Universität Göttingen (Germany) for generously providing an authentic sample of γ-rubromycin.

Abstract

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Doppelt oder nichts: In einer konvergenten Synthese der Titelverbindung, eines starken Inhibitors der humanen Telomerase, wurden zwei Pummerer-Arenreaktionen zum Aufbau des bisbenzannelierten Spiroketalgerüsts aus den beiden im Schema gezeigten Fragmenten genutzt. Die Methode bietet leichten Zugang zu einem Spektrum von substituierten bisbenzannelierten Spiroketalen ausgehend von Naphtholderivaten. MOM=Methoxymethyl.

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