Total synthesis of 4-azaeudistomin Y1 and analogues by inverse-electron demand diels-alder reactions of 3-aminoindoles with 1,3,5-triazines

Synthesis (Germany)

Volumn 45, Issue 6, 2013, Pages 743-752

  Xu, Guoxing ^a   Zheng, Lianyou ^a   Dang, Qun ^a   Bai, Xu ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

Diels Alder reactions; heterocycles; indoles; total synthesis

Indexed keywords

1 ,3 ,5-TRIAZINES; CARBOLINES; DIELS-ALDER; DIELS-ALDER REACTION; DIENOPHILES; FRIEDEL-CRAFTS ACYLATION; HETEROCYCLES; HIGH YIELD; INDOLES; INVERSE-ELECTRON DEMAND DIELS-ALDER REACTIONS; ONE-POT PROTOCOL; PROTECTING GROUP; STRUCTURE ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS;

AMIDES;

SYNTHESIS (CHEMICAL);

3 AMINOINDOLE DERIVATIVE; 4 AZAEUDISTOMIN Y1; EUDISTOMIN DERIVATIVE; INDOLE DERIVATIVE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIELS ALDER REACTION; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; PROCESS DEVELOPMENT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 84874704670     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316857     Document Type: Article

References (43)

1. Wang W. H., Nam S. J., Lee B. C., Kang H. J. Nat. Prod.: 2008; 71 163
2. Gul W., Hamann M. T. Life Sci.: 2005; 78 442
3. Won T. H., Jeon J.-e, Lee S.-H, Rho B. J., Oh K.-B, Shin J. Bioorg. Med. Chem.: 2012; 20 4082
4. Yamagishi H., Matsumoto K., Iwasaki K., Miyazaki T., Yokoshima S., Tokuyama H., Fukuyama T. Org. Lett.: 2008; 10 2369
5. Yamashita T., Kawai N., Tokuyama H., Fukuyama T. J. Am. Chem. Soc.: 2005; 127 15038
6. Dong X. C., Miao Y. P., Lin Z. G., Yu F., Wen R. Yaoxue Xuebao: 2003; 38 876
7. Bracher F., Hildebrand D., Ernst L. Arch. Pharm. (Weinheim, Ger.): 1994; 327 121
8. Panarese J. D., Waters S. P. Org. Lett.: 2010; 12 4086
9. Nissen F., Richard V., Alayrac C., Witulski B. Chem. Commun.: 2011; 47 6656
10. Balunas M. J., Kinghorn A. D. Life Sci.: 2005; 78 431
11. Haefner B. Drug Discovery Today: 2003; 8 536
12. Vuorela P., Leinonen M., Saikku P., Tammela P., Rauha J. P., Wennberg T., Vuorela H. Curr. Med. Chem.: 2004; 11 1375
13. Boger D. L. Chem. Rev.: 1986; 86 781
14. Boger D. L., Weinreb S. M. Hetero Diels-Alder Methodology in Organic Synthesis. Academic Press San Diego: 1987
15. Seitz G., Kämpchen T. Arch. Pharm. (Weinheim, Ger.): 1976; 309 679
16. Haider N. Heterocycles: 1995; 41 2519
17. Dang Q., Brown B. S., Erion M. D. J. Org. Chem.: 1996; 61 5204
18. Dang Q., Liu Y., Erion M. D. J. Am. Chem. Soc.: 1999; 121 5833
19. Lee L., Snyder J. K. In Advances in Cycloadditions. Vol. 6 Harmata M. JAI Press Stamford: 1999; 119
20. Dang Q., Liu Y., Sun Z. L. Tetrahedron Lett.: 2001; 42 8419
21. Dang Q., Gomez-Galeno J. E. J. Org. Chem.: 2002; 67 8703
22. Lahue B. R., Wan Z.-K, Snyder J. K. J. Org. Chem.: 2003; 68 4345
23. Dang Q., Carruli E., Tian F., Dang F. W., Gibson T., Li W. Y., Bai H. C., Chung M., Hecker S. J. Tetrahedron Lett.: 2009; 50 2874
24. Dang Q., Liu Y. Tetrahedron Lett.: 2009; 50 6758
25. Yu Z. X., Dang Q., Wu Y. D. J. Org. Chem.: 2001; 66 6029
26. Yu Z. X., Dang Q., Wu Y. D. J. Org. Chem.: 2005; 70 998
27. Xu G., Zheng L., Wang S., Dang Q., Bai X. Synlett: 2009; 3206
28. Salvati M. E., Balog J. A., Shan W., Giese S., Harikrishnan L. S. US 2004077606: 2004
29. Beccalli E. M., Broggini G., Martinelli M., Sottocornola S. Synthesis: 2008; 136
30. The solubilities of 1a and 1b in DMF were 1.53 and 0.06 mmol/mL, respectively; see: Xu G., Zheng L., Wang S., Dang Q., Bai X. Synth. Commun.: 2010; 40 361
31. Dess D. B., Martin J. C. J. Am. Chem. Soc.: 1991; 113 7277
32. More J. D., Finney N. S. Org. Lett.: 2002; 4 3001
33. Studer M., Blaser H.-U. J. Mol. Catal. A: Chem.: 1996; 112 437
34. Fletcher S., Gunning P. T. Tetrahedron Lett.: 2008; 49 4817
35. Murakami Y., Watanabe T., Kobayashi A., Yokoyama Y. Synthesis: 1984; 738
36. Cusack N. J., Shaw G., Litchfield G. J. J. Chem. Soc. C: 1971; 1501
37. Crystallographic data for compound 14 have been deposited with the accession number CCDC 907559 and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.
38. Glennon R. A., Von Strandtmann M. J. Heterocycl. Chem.: 1975; 12 135
39. Kitano M., Kojima A., Nakano K., Miyagishi A., Noguchi T., Ohashi N. Chem. Pharm. Bull.: 1999; 47 1538
40. Woo L. W. L, Lightowler M., Purohit A., Reed M. J., Potter B. V. L. J. Steroid Biochem. Mol. Biol.: 1996; 57 79
41. Anderson C., Freeman J., Lucas L. H., Farley M., Dalhoumi H., Widlanski T. S. Biochemistry: 1997; 36 2586
42. Lien J.-C, Jiang Y.-D, Chen C.-J, Kuo S.-C, Huang L.-J. J. Chin. Chem. Soc. (Taipei): 2008; 55 1160
43. Ebisawa M., Ueno M., Oshima Y., Kondo Y. Tetrahedron Lett.: 2007; 48 8918