Communications
[3] a) B. B. Snider, J. R. Duvall, Tetrahedron Lett. 2003, 44, 3067;
b) C. D. Monica, N. Maulucci, F. De Riccardis, I. Izzo, Tetrahe-
dron: Asymmetry 2003, 14, 3371; c) I. Izzo, E. Avallone, L. D.
Corte, N. Maulucci, F. De Riccardis, Tetrahedron: Asymmetry
2004, 15, 1181; d) S. Hara, K. Makino, Y. Hamada, Tetrahedron
2004, 60, 8031.
[4] a) J. Zhu, D. Ma, Angew.Chem. 2003, 42, 5506; Angew.Chem.
Int.Ed. 2003, 42, 5348; b) B. Zou, J. Wei, G. Cai, D. Ma, Org.
Lett. 2003, 5, 3503; c) D. Ma, Q. Wu, Tetrahedron Lett. 2001, 42,
5279; d) D. Ma, Q. Wu, Tetrahedron Lett. 2000, 41, 9089.
[5] a) P. Wipf, P. C. Fritch, J.Am.Chem.Soc. 1996, 118, 12358; b) P.
Wipf, P. C. Fritch, S. J. Geib, A. M. Sefler, J.Am.Chem.Soc.
1998, 120, 4105; c) B. McKeever, G. Pattenden, Tetrahedron
2003, 59, 2713.
[6] For other studies on the synthesis of thiazoline-containing
cyclopeptides, see: a) K. C. Nicolaou, M. Nevalainen, M. Zak,
S. Bulat, M. Bella, B. S. Safina, Angew.Chem. 2003, 42, 3540;
Angew.Chem.Int.Ed. 2003, 42, 3418; b) J. Chen, C. J. Forsyth, J.
Am.Chem.Soc. 2003, 125, 8734; c) B. McKeever, G. Pattenden,
Tetrahedron 2003, 59, 2701; d) J. M. Caba, I. M. Rodriguez, I.
Manzanares, E. Giralt, F. Albericio, J.Org.Chem. 2001, 66, 7568;
e) P. Wipf, Y. Uto, J.Org.Chem. 2000, 65, 1037.
Scheme 5. a) Et2NH, MeCN; b) [Pd(PPh3)4], N-methylaniline, CH2Cl2,
room temperature; c) BEP, iPr2NEt, CH2Cl2, 71% from 21. d) HATU,
iPr2NEt, DMF/CH2Cl2 (1:4); e) TBAF, THF; 27% (for 1) and 5% (for
23) overall yield from 22; f) TBAF, THF, 2.4:1 ratio for 1 and 23 deter-
mined by HPLC. HATU=N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-
b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophos-
phate N-oxide.
[7] a) W. F. Johns, J.Org.Chem.
1967, 32, 4086; b) W. S. Tian,
Chinese patent ZL 96116304.6.
[8] U. S. Racherla, H. C. Brown, J.Org.Chem. 1991, 56, 401.
[9] S.-I. Kiyooka, Y. Kaneko, M. Komura, H. Matsuo, M. Nakano, J.
Org.Chem. 1991, 56, 2276.
[10] J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull.
Chem.Soc.Jpn. 1979, 52, 1989.
[11] L. A. Carpino, B. J. Cohen, K. E. Stephens, S. Y. Sadat-Aalaee,
J.-H. Tien, D. C. Langridge, J.Org.Chem. 1986, 51, 3732.
[12] T. Tsunoda, S. Tatsuki, Y. Shiraishi, M. Akasaka, S. Itô,
Tetrahedron Lett. 1993, 34, 3297.
[13] a) U. Kazmaier, Angew.Chem. 1994, 106, 1046; Angew.Chem.
Int.Ed.Engl. 1994, 33, 998; b) T. Tsunoda, M. Sakai, O. Sasaki,
Y. Sako, Y. Hondo, S. Itô, Tetrahedron Lett. 1992, 33, 1651.
[14] M. A. Shalaby, C. W. Grote, H. Rappoport, J.Org.Chem. 1996,
61, 9045.
[15] P. Lafargue, P. Guenot, J. P. Lellouche, Synlett 1995, 171.
[16] M. Ciommer, H. Kunz, Synlett 1991, 593.
[17] D. S. Bose, V. Lakshminarayana, Synthesis 1999, 66.
[18] P. Li, J.-C. Xu, Tetrahedron 2000, 56, 8119.
[19] L. A. Capino, A. El-Faham, F. Albericio, Tetrahedron Lett. 1994,
35, 2279.
[20] A. Winter, B. B. Jarvis, Chemtracts: Org.Chem. 2003, 688.
antiinflammatory agents.[20] The total synthesis and structure
confirmation of halipeptin A presented herein should repre-
sent a significant step in this campaign. Further structure–
activity relationship studies are actively being pursued in this
laboratory and will be reported in due course.
Received: July 8, 2004
Keywords: amino acids · macrocyclization · natural products ·
.
peptides · total synthesis
[1] A. Randazzo, G. Bifulco, C. Giannini, M. Bucci, C. Debitus, G.
Cirino, L. Gomez-Paloma, J.Am.Chem.Soc. 2001, 123, 10870.
[2] C. D. Monica, A. Randazzo, G. Bifulco, P. Cimino, M. Aquino, I.
Izzo, F. De Riccardis, L. Gomez-Paloma, Tetrahedron Lett. 2002,
43, 5707.
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