Download PDF
Synthesis 2011(24): 4033-4036  
DOI: 10.1055/s-0031-1289594
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Straightforward Approach to Protected (S)-Dolaphenine (Doe), the Unusual Amino Acid Component of Dolastatin 10

Jens L. Burkhart, Uli Kazmaier*
Institut für Organische Chemie, Universitaet des Saarlandes, 66123 Saarbruecken, Germany
Fax: +49(681)3022409; e-Mail: u.kazmaier@mx.uni-saarland.de;
Further Information

Publication History

Received 16 September 2011
Publication Date:
07 November 2011 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

A short, four-step synthesis of Boc-protected (S)-dolaphenine is described, starting from protected phenylalanyl glycine. The key step is the cyclization of an endothiodipeptide to give a thiazolyl­ triflate, which can be subjected to a palladium-catalyzed reduction with formic acid.

Key words

dolaphenine - dolastatin - endothiopeptides - peptides - thiazoles - triflates

    References

  • 1 Pettit GR. Kamano Y. Herald CL. Tuinman AA. Boettner FE. Kizu H. Schmidt JM. Baczynskyj L. Tomer KB. Bontems RJ. J. Am. Chem. Soc.  1987,  109:  6883 
    Search in Google Scholar
  • 2 Pettit GR. Kamano Y. Fujii Y. Herald CL. Inoue M. Brown P. Gust D. Kitahara K. Schmidt JM. Doubek DL. Michel C. J. Nat. Prod.  1981,  44:  482 
    Search in Google Scholar
  • 3 Pettit GR. Kamano Y. Brown P. Gust D. Inoue M. Herald CL. J. Am. Chem. Soc.  1982,  104:  905 
    Search in Google Scholar
  • 4 Pettit GR. Kamano Y. Dufresne C. Cerny RL. Herald CL. Schmidt JM. J. Org. Chem.  1989,  54:  6005 
    Search in Google Scholar
  • 5 Pettit GR. Kamano Y. Herald CL. Dufresne C. Cerny RL. Herald DL. Schmidt JM. Kizu H. J. Am. Chem. Soc.  1989,  111:  5015 
    Search in Google Scholar
  • 6 Steube KG. Grunicke D. Pietsch T. Gignac SM. Pettit GR. Drexler HG. Leukemia  1992,  6:  1048 
    Search in Google Scholar
  • 7 Bai R. Roach MC. Jayaram SK. Barkoczy J. Pettit GR. Luduena RF. Hamel E. Biochem. Pharmacol.  1993,  45:  1503 
    Search in Google Scholar
  • 8 Pettit GR. Kamano Y. Herald CL. Fujii Y. Kizu H. Boyd MR. Boettner FE. Doubek DL. Schmidt JM. Chapuis JC. Michel C. Tetrahedron  1993,  49:  9151 
    Search in Google Scholar
  • 9 Pitot HC. McElroy EA. Reid JR. Windebank AJ. Sloan JA. Erlichman C. Bagniewski PG. Walker DL. Rubin J. Goldberg RM. Adjei AA. Ames MM. Clin. Cancer Res.  1999,  5:  525 
    Search in Google Scholar
  • 10 Madden T. Tran HT. Beck D. Huie R. Newman RA. Pusztai L. Wright JJ. Abbruzzese JL. Clin. Cancer Res.  2000,  6:  1293 
    Search in Google Scholar
  • 11 Bai R. Pettit GR. Hamel E. J. Biol. Chem.  1990,  265:  17141 
    Search in Google Scholar
  • 12 Bai R. Pettit GR. Hamel E. Biochem. Pharmacol.  1990,  39:  1941 
    Search in Google Scholar
  • 13 Bai RL. Schwartz RE. Kepler JA. Pettit GR. Hamel E. Cancer Res.  1996,  56:  4398 
    Search in Google Scholar
  • 14 Steinmetz H. Glaser N. Herdtweck E. Sasse F. Reichenbach H. Höfle G. Angew. Chem. Int. Ed.  2004,  43:  4888 ; Angew. Chem. 2004, 116, 4996
    Search in Google Scholar
  • 15 Khalil MW. Sasse F. Lunsdorf H. Elnakady YA. Reichenbach H. ChemBioChem  2006,  7:  678 
    Search in Google Scholar
  • 16 Kubicek K. Grimm SK. Orts J. Sasse F. Carlomagno T. Angew. Chem. Int. Ed.  2010,  49:  4809 ; Angew. Chem. 2010, 122, 4919
    Search in Google Scholar
  • 17 Pettit GR. Singh SB. Srirangam JK. Hoganpierson F. Williams MD. J. Org. Chem.  1994,  59:  1796 
    Search in Google Scholar
  • 18 Pettit GR. Burkett DD. Williams MD. J. Chem. Soc., Perkin Trans. 1  1996,  853 
  • 19 Pettit GR. Singh SB. Herald DL. Lloyd-Williams P. Kantoci D. Burkett DD. Barkoczy J. Hogan F. Wardlaw TR. J. Org. Chem.  1994,  59:  6287 
    Search in Google Scholar
  • 20 Pettit GR. Burkett DD. Barkoczy J. Breneman GL. Pettit WE. Synthesis  1996,  719 
  • 21 Almeida WP. Coelho F. Tetrahedron Lett.  2003,  44:  937 
    Search in Google Scholar
  • 22 Mordant C. Reymond S. Ratovelomanana-Vidal V. Genet JP. Tetrahedron  2004,  60:  9715 
    Search in Google Scholar
  • 23 Shang X. Nguyen M. Ihle NC. Synthesis  2007,  3846 
  • 24 Niel G. Roux F. Maisonnasse Y. Maugras I. Poncet J. Jouin P. J. Chem. Soc., Perkin Trans. 1  1994,  1275 
  • 25 Cella R. Venturoso RC. Stefani HA. Tetrahedron Lett.  2008,  49:  16 
    Search in Google Scholar
  • 26 Tomioka K. Satoh M. Taniyama D. Kanai M. Iida A. Heterocycles  1998,  47:  77 
    Search in Google Scholar
  • 27 Irako N. Hamada Y. Shioiri T. Tetrahedron  1992,  48:  7251 
    Search in Google Scholar
  • 28 Irako N. Hamada Y. Shioiri T. Tetrahedron  1995,  51:  12731 
    Search in Google Scholar
  • 29 Bredenkamp MW. Holzapfel CW. Synman RM. Vanzyl WJ. Synth. Commun.  1992,  22:  3029 
    Search in Google Scholar
  • 30 Pettit GR. Hogan F. Burkett DD. Singh SB. Kantoci D. Srirangam J. Williams MD. Heterocycles  1994,  39:  81 
    Search in Google Scholar
  • 31 Harrigan GG. Luesch H. Yoshida WY. Moore RE. Nagle DG. Paul VJ. Mooberry SL. Corbett TH. Valeriote FA. J. Nat. Prod.  998,  61:  1075 
    Search in Google Scholar
  • 32 Luesch H. Moore RE. Paul VJ. Mooberry SL. Corbett TH. J. Nat. Prod.  2001,  64:  907 
    Search in Google Scholar
  • 33 Mooberry SL. Leal RM. Tinley TL. Luesch H. Moore RE. Corbett TH. Int. J. Cancer  2003,  104:  512 
    Search in Google Scholar
  • 34 Sitachitta N. Rossi J. Roberts MA. Gerwick WH. Fletcher MD. Willis CL. J. Am. Chem. Soc.  1998,  120:  7131 
    Search in Google Scholar
  • 35 Nguyen VA. Willis CL. Gerwick WH. Chem. Commun.  2001,  1934 
  • 36 Kazmaier U. J. Org. Chem.  1996,  61:  3694 
    Search in Google Scholar
  • 37 Kazmaier U. Maier S. Tetrahedron  1996,  52:  941 
    Search in Google Scholar
  • 38 Krebs A. Kazmaier U. Tetrahedron Lett.  1996,  37:  7945 
    Search in Google Scholar
  • 39 Kazmaier U. Schneider C. Synthesis  1998,  1321 
  • 40 Kazmaier U. Schauss D. Pohlman M. Raddatz S. Synthesis  2000,  914 
  • 41 Ullrich A. Herrmann J. Müller R. Kazmaier U. Eur. J. Org. Chem.  2009,  6367 
  • 42 Ullrich A. Chai Y. Pistorius D. Elnakady YA. Herrmann JE. Weissman KJ. Kazmaier U. Müller R. Angew. Chem. Int. Ed.  2009,  48:  4422 ; Angew. Chem. 2009, 121, 4486
    Search in Google Scholar
  • 43 Chai Y. Pistorius D. Ullrich A. Weissman KJ. Kazmaier U. Müller R. Chem. Biol.  2010,  17:  296 
    Search in Google Scholar
  • 44 Burkhart JL. Müller R. Kazmaier U. Eur. J. Org. Chem.  2011,  3050 
  • 45 Kazmaier U. Ackermann S. Org. Biomol. Chem.  2005,  3:  3184 
    Search in Google Scholar
  • 46 Bauer M. Maurer E. Hoffmann SM. Kazmaier U. Synlett  2008,  3203 
  • 47 Kazmaier U. Persch A. Org. Biomol. Chem.  2010,  8:  5442 
    Search in Google Scholar
  • 48 Guziec FS. Wasmund LM. Tetrahedron Lett.  1990,  31:  23 
    Search in Google Scholar