Research Article

Syntheses of Prekinamycin and a Tetracyclic Quinone from Common Synthetic Intermediates

  1. Shingo Kimura1,
  2. Satoshi Kobayashi1,
  3. Takuya Kumamoto1,2,*,
  4. Aki Akagi1,
  5. Naomi Sato1,
  6. Tsutomu Ishikawa1

Article first published online: 11 APR 2011

DOI: 10.1002/hlca.201000296

Issue

Helvetica Chimica Acta

Helvetica Chimica Acta

Volume 94, Issue 4, pages 578–591, April 2011

Additional Information

How to Cite

Kimura, S., Kobayashi, S., Kumamoto, T., Akagi, A., Sato, N. and Ishikawa, T. (2011), Syntheses of Prekinamycin and a Tetracyclic Quinone from Common Synthetic Intermediates. HCA, 94: 578–591. doi: 10.1002/hlca.201000296

Author Information

  1. 1

    Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

  2. 2

    Present address: Faculty of Pharmaceutical Sciences, Musashino University, 1-1-20 Shinmachi, Nishitokyo, Tokyo 202-8585, Japan (phone/fax: +81-42-468-9278).

*Present address: Faculty of Pharmaceutical Sciences, Musashino University, 1-1-20 Shinmachi, Nishitokyo, Tokyo 202-8585, Japan (phone/fax: +81-42-468-9278).

Publication History

  1. Issue published online: 11 APR 2011
  2. Article first published online: 11 APR 2011
  3. Manuscript Received: 9 AUG 2010

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Keywords:

  • Kinamycins;
  • Prekinamycin;
  • Suzuki coupling;
  • Friedel[BOND]Crafts reaction;
  • Hydroxylation

Abstract

Towards total synthesis of a series of kinamycin and related antibiotics via common synthetic intermediates, total synthesis of prekinamycin was achieved via Suzuki coupling of naphthaleneboronic acid and bromobenzene derivative, intramolecular Friedel[BOND]Crafts reaction of 2-(naphthalen-2-yl)benzoic acid, and diazotization in ten steps from 3,5-dimethylphenol. Synthetic studies towards kinamycin antibiotics was also examined, and the tetracyclic quinone core for kinamycins was synthesized. Palladium-catalyzed site-selective hydroxylation of a benzoic acid derivative with the AB-D ring part was successfully applied to the selective D-ring functionalizations.

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