Total synthesis of a keramamide

Chemical Communications

Volumn , Issue 11, 1999, Pages 981-982

  Sowinski, Jennifer A ^a   Toogood, Peter L ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KERAMAMIDE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0033532672     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901928f     Document Type: Article

References (27)

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6. Preliminary work on this synthesis has been published: J. A. Sowinski and P. L. Toogood, Tetrahedron Lett., 1995, 36, 67.
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8. Examples of other ketoamide containing peptides see: N. Fusetani, S. Matsunaga, H. Matsumoto and Y. Y. Takebayashi, J. Am. Chem. Soc., 1990, 112, 7053; M. Hagihara and S. L. Schreiber, J. Am. Chem. Soc., 1992, 114, 6570; S. Toda, C. Kotake, T. Tsuno, Y. Narita, T. Yamasaki and M. Konishi, J. Antibiot., 1992, 45, 1580; T. Aoyagi, M. Nagai, K. Ogawa, F. Kojima, M. Okada, T. Ikeda, M. Hamada and T. Takeuchi, J. Antibiot., 1991, 44, 949; M. Nagai, K. Ogawa, Y. Muraoka, H. Naganawa, T. Aoyagi and T. Takeuchi, J. Antibiot., 1991, 44, 956.
9. Examples of other ketoamide containing peptides see: N. Fusetani, S. Matsunaga, H. Matsumoto and Y. Y. Takebayashi, J. Am. Chem. Soc., 1990, 112, 7053; M. Hagihara and S. L. Schreiber, J. Am. Chem. Soc., 1992, 114, 6570; S. Toda, C. Kotake, T. Tsuno, Y. Narita, T. Yamasaki and M. Konishi, J. Antibiot., 1992, 45, 1580; T. Aoyagi, M. Nagai, K. Ogawa, F. Kojima, M. Okada, T. Ikeda, M. Hamada and T. Takeuchi, J. Antibiot., 1991, 44, 949; M. Nagai, K. Ogawa, Y. Muraoka, H. Naganawa, T. Aoyagi and T. Takeuchi, J. Antibiot., 1991, 44, 956.
10. Examples of other ketoamide containing peptides see: N. Fusetani, S. Matsunaga, H. Matsumoto and Y. Y. Takebayashi, J. Am. Chem. Soc., 1990, 112, 7053; M. Hagihara and S. L. Schreiber, J. Am. Chem. Soc., 1992, 114, 6570; S. Toda, C. Kotake, T. Tsuno, Y. Narita, T. Yamasaki and M. Konishi, J. Antibiot., 1992, 45, 1580; T. Aoyagi, M. Nagai, K. Ogawa, F. Kojima, M. Okada, T. Ikeda, M. Hamada and T. Takeuchi, J. Antibiot., 1991, 44, 949; M. Nagai, K. Ogawa, Y. Muraoka, H. Naganawa, T. Aoyagi and T. Takeuchi, J. Antibiot., 1991, 44, 956.
11. Examples of other ketoamide containing peptides see: N. Fusetani, S. Matsunaga, H. Matsumoto and Y. Y. Takebayashi, J. Am. Chem. Soc., 1990, 112, 7053; M. Hagihara and S. L. Schreiber, J. Am. Chem. Soc., 1992, 114, 6570; S. Toda, C. Kotake, T. Tsuno, Y. Narita, T. Yamasaki and M. Konishi, J. Antibiot., 1992, 45, 1580; T. Aoyagi, M. Nagai, K. Ogawa, F. Kojima, M. Okada, T. Ikeda, M. Hamada and T. Takeuchi, J. Antibiot., 1991, 44, 949; M. Nagai, K. Ogawa, Y. Muraoka, H. Naganawa, T. Aoyagi and T. Takeuchi, J. Antibiot., 1991, 44, 956.
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21. L. A. Carpino, J. Am. Chem. Soc., 1993, 115, 4397; L. A. Carpino and A. El-Faham, J. Org. Chem., 1994, 59, 695; L. A. Carpino, A. El-Faham, C. A. Minor and F. Albericio, J. Chem. Soc., Chem. Commun., 1994, 201; L. A. Carpino, A. El-Faham and F. Albericio, Tetrahedron Lett., 1994, 35, 2279; L. A. Carpino and A. El-Faham, J. Org. Chem., 1995, 60, 3561.
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25. 1H NMR spectrum for natural KJ.
26. Chemical degradation of KG converts the homo-Ile fragment to Disoleucine indicating that KG possesses the (R) configuration at both C-13 and C-15.
27. A peak corresponding to L-alanine was also detected in this analysis, indicating that this residue did not epimerize during the cyclization reaction.