Communication

Stereoselective Total Synthsis of (±)-Urechitol A†

  1. Tatsunobu Sumiya2,
  2. Ken Ishigami Dr.1,
  3. Hidenori Watanabe Prof. Dr.1

Article first published online: 2 JUL 2010

DOI: 10.1002/anie.201002505

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 49, Issue 32, pages 5527–5528, July 26, 2010

Additional Information

How to Cite

Sumiya, T., Ishigami, K. and Watanabe, H. (2010), Stereoselective Total Synthsis of (±)-Urechitol A. Angew. Chem. Int. Ed., 49: 5527–5528. doi: 10.1002/anie.201002505

Author Information

  1. 1

    Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bukyo-ku, Tokyo 113-8657 (Japan), Fax: (+81) 3-5841-8019

  2. 2

    Research fellow from Discovery Research Laboratories, Kyorin Pharmaceutical Co., Ltd., 2399-1 Nogi, Nogi-Machi, Shimotsuga-gun, Tochigi 329-0114 (Japan)

  1. †

    We are grateful to Dr. L. M. Peña-Rodríguez for providing NMR spectra of natural urechitol A.

Publication History

  1. Issue published online: 22 JUL 2010
  2. Article first published online: 2 JUL 2010
  3. Manuscript Received: 27 APR 2010

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Keywords:

  • cycloaddition;
  • epoxides;
  • natural products;
  • total synthesis;
  • urechitol A
Thumbnail image of graphical abstract

I want to ride my tricycle: Urechitol A was synthesized as a racemate by using a [4+3] cycloaddition reaction and methanol assisted intramolecular epoxide opening as the key steps for the efficient construction of the core tricyclic framework. The overall yield was 2.3 % over 12 steps. Bn=benzyl, TES=triethylsilyl.

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