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

Jens L. Burkhart; Uli Kazmaier

doi:10.1055/s-0031-1289594

PAPER

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;

Abstract

All articles of this category

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

Full Text

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

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

3 Pettit GR. Kamano Y. Brown P. Gust D. Inoue M. Herald CL. J. Am. Chem. Soc. 1982, 104: 905

4 Pettit GR. Kamano Y. Dufresne C. Cerny RL. Herald CL. Schmidt JM. J. Org. Chem. 1989, 54: 6005

5 Pettit GR. Kamano Y. Herald CL. Dufresne C. Cerny RL. Herald DL. Schmidt JM. Kizu H. J. Am. Chem. Soc. 1989, 111: 5015

6 Steube KG. Grunicke D. Pietsch T. Gignac SM. Pettit GR. Drexler HG. Leukemia 1992, 6: 1048

7 Bai R. Roach MC. Jayaram SK. Barkoczy J. Pettit GR. Luduena RF. Hamel E. Biochem. Pharmacol. 1993, 45: 1503

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

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

10 Madden T. Tran HT. Beck D. Huie R. Newman RA. Pusztai L. Wright JJ. Abbruzzese JL. Clin. Cancer Res. 2000, 6: 1293

11 Bai R. Pettit GR. Hamel E. J. Biol. Chem. 1990, 265: 17141

12 Bai R. Pettit GR. Hamel E. Biochem. Pharmacol. 1990, 39: 1941

13 Bai RL. Schwartz RE. Kepler JA. Pettit GR. Hamel E. Cancer Res. 1996, 56: 4398

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

15 Khalil MW. Sasse F. Lunsdorf H. Elnakady YA. Reichenbach H. ChemBioChem 2006, 7: 678

16 Kubicek K. Grimm SK. Orts J. Sasse F. Carlomagno T. Angew. Chem. Int. Ed. 2010, 49: 4809 ; Angew. Chem. 2010, 122, 4919

17 Pettit GR. Singh SB. Srirangam JK. Hoganpierson F. Williams MD. J. Org. Chem. 1994, 59: 1796

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

20 Pettit GR. Burkett DD. Barkoczy J. Breneman GL. Pettit WE. Synthesis 1996, 719

21 Almeida WP. Coelho F. Tetrahedron Lett. 2003, 44: 937

22 Mordant C. Reymond S. Ratovelomanana-Vidal V. Genet JP. Tetrahedron 2004, 60: 9715

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

26 Tomioka K. Satoh M. Taniyama D. Kanai M. Iida A. Heterocycles 1998, 47: 77

27 Irako N. Hamada Y. Shioiri T. Tetrahedron 1992, 48: 7251

28 Irako N. Hamada Y. Shioiri T. Tetrahedron 1995, 51: 12731

29 Bredenkamp MW. Holzapfel CW. Synman RM. Vanzyl WJ. Synth. Commun. 1992, 22: 3029

30 Pettit GR. Hogan F. Burkett DD. Singh SB. Kantoci D. Srirangam J. Williams MD. Heterocycles 1994, 39: 81

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

32 Luesch H. Moore RE. Paul VJ. Mooberry SL. Corbett TH. J. Nat. Prod. 2001, 64: 907

33 Mooberry SL. Leal RM. Tinley TL. Luesch H. Moore RE. Corbett TH. Int. J. Cancer 2003, 104: 512

34 Sitachitta N. Rossi J. Roberts MA. Gerwick WH. Fletcher MD. Willis CL. J. Am. Chem. Soc. 1998, 120: 7131

35 Nguyen VA. Willis CL. Gerwick WH. Chem. Commun. 2001, 1934

36 Kazmaier U. J. Org. Chem. 1996, 61: 3694

37 Kazmaier U. Maier S. Tetrahedron 1996, 52: 941

38 Krebs A. Kazmaier U. Tetrahedron Lett. 1996, 37: 7945

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

43 Chai Y. Pistorius D. Ullrich A. Weissman KJ. Kazmaier U. Müller R. Chem. Biol. 2010, 17: 296

44 Burkhart JL. Müller R. Kazmaier U. Eur. J. Org. Chem. 2011, 3050

45 Kazmaier U. Ackermann S. Org. Biomol. Chem. 2005, 3: 3184

46 Bauer M. Maurer E. Hoffmann SM. Kazmaier U. Synlett 2008, 3203

47 Kazmaier U. Persch A. Org. Biomol. Chem. 2010, 8: 5442

48 Guziec FS. Wasmund LM. Tetrahedron Lett. 1990, 31: 23