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Total Synthesis of (R)-Telomestatin

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Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan, The University of Tokyo, Institute of Molecular and Cellular Biosciences, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan, and National Institute of Advanced Industrial Science and Technology (AIST), Biological Information Research Center (BIRC), Protein Network Team, Low M.W. Chemical Laboratory, AIST Tokyo Waterfront Bio-IT Research Building, 2-42 Aomi, Koto-ku, Tokyo 135-0064, Japan
Cite this: Org. Lett. 2006, 8, 18, 4165–4167
Publication Date (Web):August 9, 2006
Copyright © 2006 American Chemical Society

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    Abstract Image

    We have achieved a total synthesis of telomestatin, and its absolute configuration was determined to be (R). Coupling of cysteine-containing trisoxazole amine and serine-containing trisoxazole carboxylic acid, followed by macrocyclization, provided a 24-membered diamide. The seventh oxazole ring was formed by a Shin's procedure via dehydroamide. Cyclodehydration of a modified (R)-cysteine-(S-tBu) moiety using Kelly's method (PPh3(O)−Tf2O) with anisole furnished (R)-telomestatin, whose CD spectrum was in good agreement with that of the natural product.


    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

     Tokyo Institute of Technology.


     The University of Tokyo.

     National Institute of Advanced Industrial Science and Technology.

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    Experimental details, NMR spectra of 1216, and NMR, UV, and CD spectra of 1. This material is available free of charge via the Internet at

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