Total syntheses of eudistomins Y1-Y7 by an efficient one-pot process of tandem benzylic oxidation and aromatization of 1-benzyl-3,4-dihydro-β-carbolines

European Journal of Organic Chemistry

Volumn , Issue 16, 2013, Pages 3271-3277

  Trieu, Tien Ha ^a   Dong, Jing ^a   Zhang, Qiang ^a   Zheng, Bo ^a   Meng, Tian Zhuo ^a   Lu, Xia ^a   Shi, Xiao Xin ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Alkaloids; Aromatization; Natural products; Nitrogen heterocycles; Total synthesis

Indexed keywords

EID: 84878189387     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201300080     Document Type: Article

References (20)

1. K. L. Rinehart Jr., J. Kobayashi, G. C. Harbour, R. G. Hughes Jr, S. A. Mizsak, T. A. Scahill, J. Am. Chem. Soc. 1984, 106, 1524-1526.
2. J. Kobayashi, G. C. Harbour, J. Gilmore, K. L. Rinehart Jr., J. Am. Chem. Soc. 1984, 106, 1526-1528.
3. K. L. Rinehart Jr., J. Kobayashi, G. C. Harbour, J. Gilmore, M. Mascal, T. G. Holt, L. S. Shield, F. Lafargue, J. Am. Chem. Soc. 1987, 109, 3378-3387.
4. J. Kobayashi, H. Nakamura, Y. Ohizumi, Y. Hirata, Tetrahedron Lett. 1986, 27, 1191-1194.
5. J. Kobayashi, J.-f. Cheng, T. Ohta, S. Nozoe, Y. Ohizumi, T. Sasaki, J. Org. Chem. 1990, 55, 3666-3670.
6. O. Murata, H. Shigemori, M. Ishibashi, K. Sugama, K. Hayashi, J. Kobayashi, Tetrahedron Lett. 1991, 32, 3539-3542.
7. K. F. Kinzer, J. H. Cardellina II, Tetrahedron Lett. 1987, 28, 925-926.
8. A. Badre, A. Boulanger, E. Abou-Mansour, B. Banaigs, G. Combaut, C. Francisco, J. Nat. Prod. 1994, 57, 528-533.
9. R. A. Davis, A. R. Carroll, R. J. Quinn, J. Nat. Prod. 1998, 61, 959-960.
10. P. Schupp, T. Poehner, R. Edrada, R. Ebel, A. Berg, V. Wray, P. Proksch, J. Nat. Prod. 2003, 66, 272-275.
11. W. Wang, S.-J. Nam, B.-C. Lee, H. Kang, J. Nat. Prod. 2008, 71, 163-166.
12. T. H. Won, J.-e. Jeon, S.-H. Lee, B. J. Rho, K.-B. Oh, J. Shin, Bioorg. Med. Chem. 2012, 20, 4082-4087.
13. J. P. Kennedy, M. L. Breininger, C. W. Lindsley, Tetrahedron Lett. 2009, 50, 7067-7069.
14. W. M. Whaley, T. R. Govindachari, Org. React. 1951, 6, 74-150.
15. A. Bischler, B. Napieralski, Ber. Dtsch. Chem. Ges. 1893, 26, 1903-1908.
16. G. Fodor, S. Nagubandi, Tetrahedron 1980, 36, 1279-1300.
17. M. Movassaghi, M. D. A. Hill, Org. Lett. 2008, 10, 3485-3488.
18. L. S. Santos, R. A. Pilli, V. H. Rawal, J. Org. Chem. 2004, 69, 1283-1289.
19. M. D. Garcia, A. J. Wilson, D. P. G. Emmerson, P. R. Jenkins, Chem. Commun. 2006, 2586-2588.
20. J. Dong, X.-X. Shi, J.-J. Yan, J. Xing, Q. Zhang, S. Xiao, Eur. J. Org. Chem. 2010, 6987-6992.