A straightforward total synthesis of (-)-chaetominine

Chemistry - A European Journal

Volumn 15, Issue 32, 2009, Pages 7922-7929

  Malgesini, Beatrice ^a   Forte, Barbara ^a   Borghi, Daniela ^a   Quartieri, Francesca ^a   Gennari, Cesare ^b   Papeo, Gianluca ^a  

^a NERVIANO MEDICAL SCIENCES   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

Alkaloids; Amino acids; Lactams; Natural products; Total synthesis

Indexed keywords

ACYLIMINIUM ION; ALKALOIDS; CANCER CELL LINES; D-RINGS; D-TRYPTOPHAN; DIASTEREOISOMERS; DOUBLE BONDS; HYDROXY GROUPS; INDOLE RINGS; INHIBITORY ACTIVITY; LACTAMS; LATE STAGE; METHYL ESTERS; NATURAL PRODUCTS; PROTECTIVE GROUP; RING JUNCTION; STEREOCONTROL; SYNTHETIC STRATEGIES; TOTAL SYNTHESIS; TRIPEPTIDE;

AMIDES; AMINATION; AMINES; AMINO ACIDS; CELL CULTURE; CELL MEMBRANES; ESTERS; ORGANIC ACIDS;

SYNTHESIS (CHEMICAL);

CHAETOMININE; CYCLOPEPTIDE; FUMIQUINAZOLINE A; INDOLE ALKALOID; KAPAKAHINE B; QUINAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG SCREENING; HUMAN; STEREOISOMERISM; SYNTHESIS;

DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC; QUINAZOLINES; STEREOISOMERISM;

EID: 68349101069     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900793     Document Type: Article

References (51)

1. H. W. Zhang, Y. C. Song, R. X. Tan, Nat. Prod Rep. 2006, 23, 753-771.
2. B. P. Bashyal, E. M. K. Wijeratne, S. H. Faeth, A. A. L. Gunatilaka, J. Nat. Prod. 2005, 68, 724-728.
3. G. A. Strobel, A. Stierle, D. Stierle, W. M. Hess, Mycotoxins 1993, 47, 71- 78.
4. R. X. Tan, P. R. Jensen, P. G. Williams, W. Fenical, J. Nat. Prod. 2004, 67, 1374-1382.
5. S. Safe, A. Taylor, J. Chem. Soc. Perkin Trans. 11972, 472-479.
6. D. Hauser, H. P. Weber, H. P. Sigg, Helv. Chim. Acta 1970, 53, 1061- 1073.
7. a) S. Sekita, K. Yoshihira, S. Natori, H. Kuwano, Tetrahedron Lett. 1973, 14, 2109-2112;
8. b) S. Sekita, K. Yoshihira, S. Natori, H. Kuwano, Tetrahedron Lett. 1976, 17, 1351-1354;
9. c) S. Sekita, K. Yoshihira, S. Natori, H. Kuwano, Tetrahedron Lett. 1977, 18, 2771-2774;
10. d) W. Jiao, Y. Feng, J. W. Blunt, A. L. J. Cole, M. H. G. Munro, J. Nat. Prod. 2004, 67, 1722-1725;
11. e) G. Ding, Y. C. Song, J. R. Chen, C. Xu, H. M. Ge, X. T. Wang, R. X. Tan, J. Nat. Prod. 2006, 69, 302-304.
12. Y. Itoh, K. Kodama, K. Furuya, S. Takahashi, T. Haneishi, Y Takiguchi, M. Arai, J. Antibiot. 1980, 33, 468-473.
13. M. Kobayashi, R. Kanasaki, I. Sato, F. Abe, K. Nitta, M. Ezaki, K. Sakamoto, M. Hashimoto, A. Fujie, M. Hino, Y. Hori, Biosci. Biotechnol. Biochem. 2005, 69, 515-521.
14. O. Schlörke, A. Zeeck, Eur. J. Org. Chem. 2006, 1043-1049.
15. R. H. Jiao, S. Xu, J. Y Liu, H. M. Ge, H. Ding, C. Xu, H. L. Zhu, R. X. Tan, Org. Lett. 2006, 8, 5709-5712.
16. a) M. Yamazaki, H. Fujimoto, E. Okuyama, Chem. Pharm. Bull. 1978, 26, 111-117;
17. b) J. Clardy, J. P. Springer, G. Büchi, K. Matsuo, R. Wightman, J. Am. Chem. Soc. 1975, 97, 663-665;
18. c) M. R. Ariza, T. O. Larsen, B. O. Peterson, J. O. Duus, A. F. Barrero, J. Agric. Food Chem. 2002, 50, 6361-6365.
19. a) A. Numata, C. Takahashi, T. Matsushita, T. Miyamoto; K. Kawai, Y Usami, E. Matsumura, M. Inoue, H. Ohishi, T. Shingu, Tetrahedron Lett. 1992, 33, 1621-1624;
20. K. Kawai, Y Usami, E. Matsumura, M. Inoue, H. Ohishi, T. Shingu, Tetrahedron Lett. 1992, 33, 1621-1624;
21. b) C. Takahashi, T. Matsushita, M. Doi, K. Minoura, T. Shingu, Y Kumeda, A. Numata, J. Chem. Soc. Perkin Trans. 1 1995, 2345-2353;
22. c) G. N Belofsky, M. Anguera, P. R. Jensen, W. Fenical, M. Köck, Chem. Eur. J. 2000, 6, 1355-1360;
23. d) S.-M. Wong, L. L. Musza, G. C. Kydd, R. Kullnig, A. M. Gillum, R. Cooper, J. Antibiot. 1993, 46, 545-553.
24. a) B. K. S. Yeung, Y Nakao, R. B. Kinnel, J. R. Carney, W. Y. Yoshida, P. J. Scheuer, J. Org. Chem. 1996, 61, 7168-7173;
25. b) Y. Nakao, J. Kuo, W. Y. Yoshida, M. Kelly, P. J. Scheuer, Org. Lett. 2003, 5, 1387-1390.
26. B. B. Snider, H. Zeng, J. Org. Chem. 2003, 68, 545-563.
27. B. B. Snider, X. Wu, Org. Lett. 2007, 9, 4913-4915.
28. M. Toumi, F. Couty, J. Marrot, G. Evano, Org. Lett. 2008, 10, 5027-5030.
29. E. R. Radwanski, R. L. Last, Plant Cell 1995, 7, 921-934.
30. a)R.W. Hoffmann, Synthesis 2006, 3531-3541;
31. b) P. S. Baran, T. J. Maimone, J. M. Richter, Nature 2007, 446, 404-408;
32. c) K. Gademann, S. Bonazzi, Angew. Chem. 2007, 119, 5754-5756;
33. Angew. Chem. Int. Ed. 2007, 46, 5656-5658;
34. d) A. K. Yudin, R. Hili, Chem. Eur. J. 2007,13, 6538-6542;
35. e) N. Z. Burns, P. S. Baran, R. W. Hoffmann, Angew. Chem. 2009, 121, 2896-2910;
36. Angew. Chem. Int. Ed. 2009, 48, 2854-2867.
37. a) H. Wang, A. Ganesan, J. Org. Chem. 1998, 63, 2432-2433;
38. b) M. Nakagawa, M. Taniguchi, M. Sodeoka, M. Ito, K. Yamaguchi, T. Hino, J. Am. Chem. Soc. 1983, 105, 3709-3710.
39. A slightly decreased yield (85%) was observed during the scale-up of the coupling reaction, mainly due to some self-condensation of anthranilic acid.
40. a) W. König, R. Geiger, Chem. Ber. 1970, 103, 2034-2040;
41. b) S. C. Moratti, 3-Hydroxy-l,2,3-benzotriazin-4(3H)-one, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001.
42. 1HNMR analysis of the crude amide diastereoisomeric mixture (17) (see Supporting Information).
43. a) M. Ohno, T. F. Spande, B. Witkop, J. Am. Chem. Soc. 1970, 92, 343-348;
44. b) M. Okada, I. Sato, S. J. Cho, D. Dubnau, Y Sakagami, Tetrahedron 2006, 62, 8907-8918.
45. a) F. A. Davis, J. C. Towson, D. B. Vashi, R. ThimmaReddy, J. P. McCauley, M. E. Harakal, D. J. Gosciniak, J. Org. Chem. 1990, 55, 1254-1261;
46. b) Org. Synth. 1993, 8, 546;
47. Org. Synth. 1988, 66, 203.
48. F. He, B. M. Foxman, B. B. Snider, J. Am. Chem. Soc. 1998, 120, 6417-6418.
49. a) J. L. Fry, R. J. Rahaim, Jr., R. E. MaleczkaJr., Triethylsilane, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001;
50. b)D.N Kursanov, Z. N. Pames, N. M. Loim, Synthesis 1974, 633-651.
51. M. Colombo, F. Riccardi-Sirtori, V. Rizzo, Rapid Commun. Mass Spectrom. 2004, 18, 511-517.