Synthesis of small cyclic peptides via intramolecular Heck reactions

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 353-356

  Reddy, P Rajamohan ^b   Balraju, V ^b   Madhavan, G R ^b   Banerji, Biswadip ^a   Iqbal, Javed ^a,b,c  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b DR REDDY'S LABORATORIES LTD   (India)

^c REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; FUNCTIONAL GROUP; SYNTHETIC PEPTIDE; TRIPEPTIDE;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CYCLIZATION; DRUG SYNTHESIS; HECK REACTION; HYDROGEN BOND; MOLECULAR DYNAMICS; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 15444365760     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02573-X     Document Type: Article

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17. For a general Heck coupling reaction, see: (a) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083; (b) Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133; (c) Patel, B. A.; Ziegler, C. B.; Cortese, N. A.; Plevyak, J. E.; Zebovitz, T. C.; Terpko, M.; Heck, R. F. J. Org. Chem. 1977, 42, 3903-3907; (d) Beletskaya, I.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Grisp, G. T. Chem. Soc. Rev. 1998, 27, 427; (f) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998; (g) Link, J. T.; Overman, L. E. Chemtech. 1998, 28, 19; (h) Negishi, E.; Ma, M.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922-1923.
18. For a general Heck coupling reaction, see: (a) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083; (b) Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133; (c) Patel, B. A.; Ziegler, C. B.; Cortese, N. A.; Plevyak, J. E.; Zebovitz, T. C.; Terpko, M.; Heck, R. F. J. Org. Chem. 1977, 42, 3903-3907; (d) Beletskaya, I.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Grisp, G. T. Chem. Soc. Rev. 1998, 27, 427; (f) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998; (g) Link, J. T.; Overman, L. E. Chemtech. 1998, 28, 19; (h) Negishi, E.; Ma, M.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922-1923.
19. For a general Heck coupling reaction, see: (a) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083; (b) Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133; (c) Patel, B. A.; Ziegler, C. B.; Cortese, N. A.; Plevyak, J. E.; Zebovitz, T. C.; Terpko, M.; Heck, R. F. J. Org. Chem. 1977, 42, 3903-3907; (d) Beletskaya, I.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Grisp, G. T. Chem. Soc. Rev. 1998, 27, 427; (f) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998; (g) Link, J. T.; Overman, L. E. Chemtech. 1998, 28, 19; (h) Negishi, E.; Ma, M.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922-1923.
20. For a general Heck coupling reaction, see: (a) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083; (b) Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133; (c) Patel, B. A.; Ziegler, C. B.; Cortese, N. A.; Plevyak, J. E.; Zebovitz, T. C.; Terpko, M.; Heck, R. F. J. Org. Chem. 1977, 42, 3903-3907; (d) Beletskaya, I.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Grisp, G. T. Chem. Soc. Rev. 1998, 27, 427; (f) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998; (g) Link, J. T.; Overman, L. E. Chemtech. 1998, 28, 19; (h) Negishi, E.; Ma, M.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922-1923.
21. For a general Heck coupling reaction, see: (a) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083; (b) Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133; (c) Patel, B. A.; Ziegler, C. B.; Cortese, N. A.; Plevyak, J. E.; Zebovitz, T. C.; Terpko, M.; Heck, R. F. J. Org. Chem. 1977, 42, 3903-3907; (d) Beletskaya, I.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Grisp, G. T. Chem. Soc. Rev. 1998, 27, 427; (f) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998; (g) Link, J. T.; Overman, L. E. Chemtech. 1998, 28, 19; (h) Negishi, E.; Ma, M.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922-1923.
22. For a general Heck coupling reaction, see: (a) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083; (b) Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133; (c) Patel, B. A.; Ziegler, C. B.; Cortese, N. A.; Plevyak, J. E.; Zebovitz, T. C.; Terpko, M.; Heck, R. F. J. Org. Chem. 1977, 42, 3903-3907; (d) Beletskaya, I.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Grisp, G. T. Chem. Soc. Rev. 1998, 27, 427; (f) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998; (g) Link, J. T.; Overman, L. E. Chemtech. 1998, 28, 19; (h) Negishi, E.; Ma, M.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922-1923.
23. For a general Heck coupling reaction, see: (a) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083; (b) Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133; (c) Patel, B. A.; Ziegler, C. B.; Cortese, N. A.; Plevyak, J. E.; Zebovitz, T. C.; Terpko, M.; Heck, R. F. J. Org. Chem. 1977, 42, 3903-3907; (d) Beletskaya, I.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009; (e) Grisp, G. T. Chem. Soc. Rev. 1998, 27, 427; (f) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998; (g) Link, J. T.; Overman, L. E. Chemtech. 1998, 28, 19; (h) Negishi, E.; Ma, M.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922-1923.
24. -1.
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27. D=+98 (c 0.25, MeOH).