Zuschrift

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

  1. Shuji Akai Prof. Dr.1,2,
  2. Keisuke Kakiguchi Dr.1,
  3. Yuka Nakamura1,
  4. Ikumi Kuriwaki1,
  5. Toshifumi Dohi Dr.1,
  6. Shusaku Harada1,
  7. Ozora Kubo1,
  8. Nobuyoshi Morita Dr.1,3,
  9. Yasuyuki Kita Prof. Dr.1

Article first published online: 14 AUG 2007

DOI: 10.1002/ange.200702382

Issue

Angewandte Chemie

Angewandte Chemie

Volume 119, Issue 39, pages 7602–7605, October 1, 2007

Additional Information

How to Cite

Akai, S., Kakiguchi, K., Nakamura, Y., Kuriwaki, I., Dohi, T., Harada, S., Kubo, O., Morita, N. and Kita, Y. (2007), Total Synthesis of (±)-γ-Rubromycin on the Basis of Two Aromatic Pummerer-Type Reactions. Angewandte Chemie, 119: 7602–7605. doi: 10.1002/ange.200702382

Author Information

  1. 1

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

  2. 2

    Current Address: School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan

  3. 3

    Current Address: Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan

  1. †

    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.

Publication History

  1. Issue published online: 20 SEP 2007
  2. Article first published online: 14 AUG 2007
  3. Manuscript Received: 1 JUN 2007

Funded by

  • Ministry of Education, Culture, Sports, Science and Technology, Japan

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Keywords:

  • Naturstoffe;
  • Pummerer-Reaktion;
  • Spiroketale;
  • Totalsynthesen;
  • Umlagerungen

Graphical 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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