Total synthesis of (-)-Lycoperine a

Organic Letters

Volumn 12, Issue 1, 2010, Pages 72-75

  Rychnovsky, Scott D ^a   Nakamura, Yoshitaka ^a   Burke, Anthony M ^a   Kotani, Shunsuke ^a   Ziller, Joseph W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; LYCOPERINE A; QUINOLINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; LYCOPODIUM; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; ALKYLATION; CYCLIZATION; LYCOPODIUM; MOLECULAR STRUCTURE; QUINOLINES; STEREOISOMERISM;

EID: 73949084123     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902389e     Document Type: Article

References (35)

1. Ma, X.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752-772.
2. (a) Tang, X. C.; Han, Y. F.; Chen, X. P.; Zhu, X. D. Acta Pharmacol. Sin. 1986, 7, 507-511.
3. (b) Tang, X. C.; De Sarno, P.; Sugaya, K.; Giacobini, E. J. Neurosci. Res. 1989, 24, 276-285.
4. Qian, L.; Ji, R. Tetrahedron Lett. 1989, 30, 2089-2090.
5. (a) Zhang, R. W.; Tang, X. C.; Han, Y. Y.; Sang, G. W.; Zhang, Y. D.; Ma, Y. X.; Zhang, C. L.; Yang, R. M. Acta Pharmacol. Sin. 1991, 12, 250-252.
6. (b) Jiang, H. L.; Luo, X. M.; Bai, D. L. Curr. Med. Chem. 2003, 10, 2231-2252.
7. Ayer, W. A.; Trifonov, L. S. LycopodiumAlkaloids; Academic Press: San Diego, 1994.
8. Bisai, A.; West, S. P.; Sarpong, R. J. Am. Chem. Soc. 2008, 130, 7222-7223.
9. Bodeker, K. Justus Liebigs Ann. Chem. 1881, 208, 363.
10. Nyembo, L.; Goffin, A.; Hootele, C.; Jean Claude, B. Can. J. Chem. 1978, 56, 851-856.
11. Hirasawa, Y.; Kobayashi, J.; Morita, H. Org. Lett. 2006, 8, 123-126.
12. Husson, H.-P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383-394.
13. (a) Noël, R.; Vanucci-Bacque, C.; Fargeau-Bellassoued, M.-C.; Lhommet, G. J. Org. Chem. 2005, 70, 9044-9047.
14. (b) Noel, R.; Fargeau-Bellassoued, M. C.; Vanucci-Bacque, C.; Lhommet, G. Synthesis 2008, 1948-1954.
15. (c)Noel, R.; Vanucci-Bacque, C.; Fargeau-Bellassoued, M. C.; Lhommet, G. Eur. J. Org. Chem. 2007, 476-486.
16. (a) Amat, M.; Fabregat, R.; Griera, R.; Bosch, J. J. Org. Chem. 2009, 74, 1794-1797.
17. (b) Amat, M.; Perez, M.; Minaglia, A. T.; Bosch, J. J. Org. Chem. 2008, 73, 6920-6923.
18. (c)Amat, M.; Griera, R.; Tabregat, R.; Molins, E.; Bosch, J. Angew. Chem., Int. Ed. 2008, 47, 3348-3351.
19. (d)Amat, M.; Bassas, O.; Llor, N.; Canto, M.; Perez, M.; Molins, E.; Bosch, J. Chem.-Eur. J. 2006, 12, 7872-7881.
20. (e) Escolano, C.; Amat, M.; Bosch, J. Chem-Eur. J. 2006, 12, 8198-8207.
21. Details of the X-ray structures for compounds 11, 12, and 13 are included in Supporting Information.
22. (a)Bartoli, G.; Cimarelli, C.; Palmieri, G. J. Chem. Soc., Perkin Trans. 1 1994, 537-543. Hsung et al. utilized Palmieri's method for the total synthesis of (±)-tangutorine; see:
23. (b) Luo, S.; Zificsak, C. A.; Hsung, R. P. Org. Lett. 2003, 5, 4709-4712.
24. Mori, M.; Nakanishi, M.; Kajishima, D.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 9801-9807.
25. No epimerization was detected in the generation of enol triflate 14 at -78°C, but significant epimerization was observed at -35°C.
26. Baillargeon, V. P.; Stille, J. K. J. Am. Chem. Soc. 2002, 108, 452-461.
27. Mori, M.; Chiba, K.; Okita, M.; Kayo, I.; Ban, Y. Tetrahedron 1985, 41, 375-385.
28. Bonin, M.; Chiaroni, A.; Riche, C.; Beloeil, J.-C.; Grierson, D. S.; Husson, H.-P. J. Org. Chem. 1987, 52, 382-385.
29. Takahashi et al. reported the bisalkylation of 1-benzyl-2,6- dicyanopiperidine in a stepwise manner; see: Takahashi, K.; Kurita, H.; Ogura, K.; Iida, H. J. Org. Chem. 1985, 50, 4368-4371.
30. (a) Boucher, J.-L.; Stella, L. Tetrahedron 1985, 41, 875-887.
31. (b) Enders, D.; Shilvock, J. P.; Raabe, G. J. Chem. Soc., Perkin Trans. 1 1999, 1617-1619.
32. Abe, K.; Okumura, H.; Tsugoshi, T.; Nakamura, N. Synthesis 1984, 597-598.
33. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849-3862.
34. 24 -196 (c 0.14 MeOH).
35. 13C NMR data shows all peaks within 0.5 ppm of reported values and an average difference of 0.14 ppm.