Synthesis of Cyclotheonamide B and Its Derivatives

Authors

  • Jingen Deng,

    1. Department of Synthetic Organic Chemistry, Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467 (Japan), Telefax: Int. code + (52) 834-4172
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  • Prof. Dr. Yasumasa Hamada,

    1. Department of Synthetic Organic Chemistry, Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467 (Japan), Telefax: Int. code + (52) 834-4172
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  • Prof. Dr. Takayuki Shioiri,

    Corresponding author
    1. Department of Synthetic Organic Chemistry, Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467 (Japan), Telefax: Int. code + (52) 834-4172
    • Department of Synthetic Organic Chemistry, Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467 (Japan), Telefax: Int. code + (52) 834-4172
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  • Dr. Shigeki Matsunaga,

    1. Laboratory of Marine Biochemistry, Faculty of AGriculture, The University of Tokyo, Yayoi, Bunkyoku, Tokyo 113 (Japan)
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  • Prof. Dr. Nobuhiro Fusetani

    1. Laboratory of Marine Biochemistry, Faculty of AGriculture, The University of Tokyo, Yayoi, Bunkyoku, Tokyo 113 (Japan)
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  • This work was supported in part by the Ministry of Education, Science and Culture. Japan. One of the authors (J. D.) is grateful to the Japan Society for the Promotion of Science for the postgraduate fellowship.

Abstract

original image

A high-yielding macrolactonization is the key step in the convergent synthesis of the macrocyclic pentapeptide 1. The hydroxy derivatives 1b and 1c are not inhibitors of serine protease, since they do not have the α-carbonylamide unit (X, Y [DOUBLE BOND] O) found in the naturally occurring cyclotheonamide B (1a).

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