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

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2011(24): 4033-4036
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;

Further Information

Publication History

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

Abstract
Full Text
References

Permissions and Reprints 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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Google Scholar
18 Pettit GR. Burkett DD. Williams MD. J. Chem. Soc., Perkin Trans. 1 1996, 853

Google Scholar
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

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

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

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

Google Scholar
23 Shang X. Nguyen M. Ihle NC. Synthesis 2007, 3846

Google Scholar
24 Niel G. Roux F. Maisonnasse Y. Maugras I. Poncet J. Jouin P. J. Chem. Soc., Perkin Trans. 1 1994, 1275

Google Scholar
25 Cella R. Venturoso RC. Stefani HA. Tetrahedron Lett. 2008, 49: 16

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

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

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

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

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

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

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

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

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

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

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

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

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

Google Scholar
39 Kazmaier U. Schneider C. Synthesis 1998, 1321

Google Scholar
40 Kazmaier U. Schauss D. Pohlman M. Raddatz S. Synthesis 2000, 914

Google Scholar
41 Ullrich A. Herrmann J. Müller R. Kazmaier U. Eur. J. Org. Chem. 2009, 6367

Google Scholar
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

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

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

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

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

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

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

Google Scholar