Total syntheses of leuconoxine, leuconodine B, and melodinine e by oxidative cyclic aminal formation and diastereoselective ring-closing metathesis

Organic Letters

Volumn 16, Issue 9, 2014, Pages 2526-2529

  Umehara, Atsushi ^a   Ueda, Hirofumi ^a   Tokuyama, Hidetoshi ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID; LEUCONODINE B; LEUCONOXINE; MELODININE E; RAUWOLFIA ALKALOID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SECOLOGANIN TRYPTAMINE ALKALOIDS; STEREOISOMERISM;

EID: 84899820295     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500903e     Document Type: Article

References (45)

1. Abe, F.; Yamauchi, T. Phytochemistry 1994, 35, 169
2. Gan, C.-Y.; Low, Y.-Y.; Thomas, N. F.; Kam, T.-S. J. Nat. Prod. 2013, 76, 957
3. This compound was also isolated by Luo and co-workers from the other Apocynaceae plant, Alstonia schlaris, and was named (-)-scholarisine G: Feng, T.; Cai, X.-H.; Zhao, P.-J.; Du, Z.-Z.; Li, W.-Q.; Luo, X.-D. Planta Med. 2009, 75, 1537
4. Feng, T.; Cai, X.-H.; Liu, Y.-P.; Li, Y.; Wang, Y.-Y.; Luo, X.-D. J. Nat. Prod. 2010, 73, 22
5. Low, Y.-Y.; Hong, F.-J.; Lim, K.-H.; Thomas, N. F.; Kam, T.-S. J. Nat. Prod. 2014, 77, 327
6. David, B.; Sévenet, T.; Thoisn, O.; Awang, K.; Pais, M.; Wright, M.; Guénard, D. Bioorg. Med. Chem. Lett. 1997, 7, 2155
7. Baudoin, O.; Guénard, D.; Guéritte, F. Mini-Rev. Org. Chem. 2004, 1, 333 and references therein
8. Décor, A.; Bellocq, D.; Thoison, O.; Lekieffre, N.; Chiaroni, A.; Ouazzani, J.; Cresteil, T.; Guéritte, F.; Baudoin, O. Bioorg. Med. Chem. 2006, 14, 1558
9. Linde, H. H. A. Helv. Chim. Acta 1965, 48, 1822
10. Abraham, D. J.; Rosenstein, R. D.; Lyon, R. L.; Fong, H. H. S. Tetrahedron Lett. 1972, 13, 909
11. Ratcliffe, A. H.; Smith, G. F.; Smith, G. N. Tetrahedron Lett. 1973, 52, 5179
12. Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2000, 122, 6321
13. Magnus, P.; Rainey, T. Tetrahedron 2001, 57, 8647
14. Bowíe, A. L.; Hughes, C. C.; Trauner, D. Org. Lett. 2005, 7, 5207
15. Johnson, J. A.; Li, N.; Sames, D. J. Am. Chem. Soc. 2002, 124, 6900
16. Liu, Z.; Wasmuth, A. S.; Nelson, S. G. J. Am. Chem. Soc. 2006, 128, 10352
17. Banwell, M. G.; Beck, D. A. S.; Willis, A. C. ARKIVOC 2006, 163
18. Gu, Z.; Zakarian, A. Org. Lett. 2010, 12, 4224
19. Sugimoto, K.; Toyoshima, K.; Nonaka, S.; Kotaki, K.; Ueda, H.; Tokuyama, H. Angew. Chem., Int. Ed. 2013, 52, 7168
20. David, B.; Sévenet, T.; Morgat, M.; Guénard, D.; Moisand, A.; Tollon, Y.; Thoison, O.; Wright, M. Cell Motil. Cytoskeleton 1994, 28, 317
21. Kam, T.-S.; Subramaniam, G.; Lim, K.-H.; Choo, Y.-M. Tetrahedron Lett. 2004, 45, 5995
22. Magolan, J.; Carson, C. A.; Kerr, M. A. Org. Lett. 2008, 10, 1437
23. Lv, Z.; Li, Z.; Liang, G. Org. Lett. 2014, 16, 1653
24. Biechy, A.; Zard, S. Z. Org. Lett. 2009, 11, 2800
25. Zhong, X.; Li, Y.; Han, F.-S. Chem.-Eur. J. 2012, 18, 9784
26. Nakajima, R.; Ogino, T.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2010, 132, 1236
27. Iwama, Y.; Okano, K.; Sugimoto, K.; Tokuyama, H. Org. Lett. 2012, 14, 2320
28. Iwama, Y.; Okano, K.; Sugimoto, K.; Tokuyama, H. Chem.-Eur. J. 2013, 19, 9325
29. Xu, Z.; Wang, Q.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 19127
30. Kamenecka, T. M.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 2995
31. Baran, P. S.; Cuerrero, C. A.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 5628
32. Kajiyama, D.; Saitoh, T.; Yamaguchi, S.; Nishiyama, S. Synthesis 2012, 1667
33. Fukuda, Y.; Shindo, M.; Shishido, K. Org. Lett. 2003, 5, 749
34. For a review on the intramolecular Mizoroki-Heck reaction, see: Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945
35. Tokuyama, H.; Kaburagi, Y.; Chen, X.; Fukuyama, T. Synthesis 2000, 429
36. Tokuyama, H.; Fukuyama, T. Chem. Rec. 2002, 2, 37
37. Van der Ende, A. E.; Kravitz, E. J.; Harth, E. J. Am. Chem. Soc. 2008, 130, 8706
38. Campbell, E. L.; Zuhl, A. M.; Liu, C. M.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 3009
39. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488
40. Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485
41. A selected report on the oxidation of indoles with DMDO, see: Schkeryantz, J. M.; Woo, J. C. G.; Siliphaivanh, P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 11964
42. Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919
43. Movassaghi, M.; Schmidt, M. A.; Ashenhurst, J. A. Org. Lett. 2008, 10, 4009
44. Downey, C. D.; Fleisher, A. S.; Rague, J. T.; Safran, C. L.; Venable, M. E.; Pike, R. D. Tetrahedron Lett. 2011, 52, 4756
45. Garber, S.; Kingsbury, J.; Gray, B.; Hoveyda, A. J. Am. Chem. Soc. 2000, 122, 8168