Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated α-aminonitrile

Journal of Organic Chemistry

Volumn 73, Issue 12, 2008, Pages 4526-4531

  Liermann, Johannes C ^a,b   Opatz, Till ^a,b  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL REACTIONS; COMPLEXATION; ETHERS; FUNCTION EVALUATION; HYDROCARBONS; MICROFLUIDICS; NUMERICAL METHODS; ORGANIC COMPOUNDS; PHENOLS; PIGMENTS; TELLURIUM COMPOUNDS;

(I ,J) CONDITIONS; (MIN ,MAX ,+) FUNCTIONS; AMERICAN CHEMICAL SOCIETY (ACS); CARBONITRILES; CHEMICAL EQUATIONS; DIHYDROISOQUINOLINES; ISOQUINOLINES; LAMELLARIN; ONE POT SYNTHESIS; PROTECTING GROUPS (PG); REACTION SEQUENCES; STARTING MATERIALS; SYNTHESIS (OF CHIRAL IONIC LIQUIDS); TETRAHYDROISOQUINOLINE (THIQ);

SYNTHESIS (CHEMICAL);

1 BENZYL 3,4 DIHYDROISOQUINOLINE; 1,2,3,4 TETRAHYDROISOQUINOLINE 1 CARBONITRILE; AMINONITRILE; ETHER DERIVATIVE; LAMELLARIN G; LAMELLARIN U; NITRILE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; LACTONIZATION; ONE POT SYNTHESIS; PROTON TRANSPORT; REACTION ANALYSIS;

ALKYLATION; COUMARINS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; ISOQUINOLINES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; NITRILES; SPECTROPHOTOMETRY, INFRARED;

EID: 45249122015     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800467e     Document Type: Article

References (38)

1. Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155-156.
2. Andersen, R. J.; Faulkner, D. J.; He, C. H.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492-5495.
3. Faulkner, D. J. Nat. Prod. Rep. 1998, 15, 113-158.
4. Bailly, C. Curr. Med. Chem. 2004, 4, 363-378.
5. Fan, H.; Peng, J.-N.; Hamann, M. T.; Hu, J.-F. Chem. Rev. 2008, 108, 264-287.
6. Facompré, M.; Tardy, C.; Bal-Mahieu, C.; Colson, P.; Perez, C.; Manzanares, I.; Cuevas, C.; Bailly, C. Cancer Res. 2003, 63, 7392-7399.
7. Reddy, M. V.; Rao, M. R.; Rhodes, D.; Hansen, M. S.; Rubins, K.; Bushman, F. D.; Venkateswarlu, Y.; Faulkner, D. J. J. Med. Chem. 1999, 42, 1901-1907.
8. Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951-5962.
9. Banwell, M.; Flynn, B.; Hockless, D. Chem. Commun. 1997, 2259-2260.
10. Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363-1366.
11. Ploypradith, P.; Mahidol, C.; Sahakitpichan, P.; Wongbundit, S.; Ruchirawat, S. Angew. Chem., Int. Ed. 2004, 43, 866-868.
12. Ploypradith, P.; Kagan, R. K.; Ruchirawat, S. J. Org. Chem. 2005, 70, 5119-5125.
13. Ploypradith, P.; Petchmanee, T.; Sahakitpichan, P.; Litvinas, N. D.; Ruchirawat, S. J. Org. Chem. 2006, 71, 9440-9448.
14. Handy, S. T.; Zhang, Y. N.; Bregman, H. J. Org. Chem. 2004, 69, 2362-2366.
15. Pla, D.; Marchal, A.; Olsen, C. A.; Albericio, F.; Álvarez, M. J. Org. Chem. 2005, 70, 8231-8234.
16. Meyer, N.; Opatz, T. Eur. J. Org. Chem. 2006, 3997-4002.
17. Meyer, N.; Opatz, T. Synlett 2003, 1427-1430.
18. Meyer, N.; Werner, F.; Opatz, T. Synthesis 2005, 945-956.
19. Kison, C.; Meyer, N.; Opatz, T. Angew. Chem., Int. Ed. 2005, 44, 5662-5664.
20. Kobor, J.; Koczka, K. Szegedi Tanarkepzo Foiskola Tudomanyos Kozlemenyei 1969, 179-183.
21. Werner, F.; Blank, N.; Opatz, T. Eur. J. Org. Chem. 2007, 3911-3915.
22. von Miller, W.; Plöchl, J. Ber. Dtsch. Chem. Ges. 1898, 31, 2718-2720.
23. Reimer, M.; Tobin, E.; Schaffner, M. J. Am. Chem. Soc. 1935, 57, 211-215.
24. Grob, C. A.; Camenisch, K. Helv. Chim. Acta 1953, 36, 49-58.
25. Kapadia, G. J.; Shah, N. J.; Highet, R. J. J. Pharm. Sci. 1964, 53, 1431-1432.
26. Dauzonne, D.; Royer, R. Synthesis 1987, 399-401.
27. Peschko, C.; Winklhofer, C.; Terpin, A.; Steglich, W. Synthesis 2006, 3048-3057.
28. Bischler, A.; Napieralski, B. Ber. Dtsch. Chem. Ges. 1893, 26, 1903-1908.
29. Clezy, P. S.; Salek, A. Aust. J. Chem. 1996, 49, 265-272.
30. Pictet, A.; Finkelstein, M. Ber. Dtsch. Chem. Ges. 1909, 42, 1979-1989.
31. Pinza, M.; Dorigotti, L.; Pifferi, G. Eur. J. Med. Chem. 1976, 11, 395-398.
32. Perales, J. B.; Makino Narubumi, F.; Van Vranken, D. L. J. Org. Chem. 2002, 67, 6711-6717.
33. Mujahidin, D.; Doye, S. Eur. J. Org. Chem. 2005, 2689-2693.
34. Yamaguchi, S.; Tsuchida, N.; Miyazawa, M.; Hirai, Y. J. Org. Chem. 2005, 70, 7505-7511.
35. Lehnert, W. Tetrahedron 1972, 28, 663-666.
36. Reddy, M. V. R.; Faulkner, D. J.; Venkateswarlu, Y.; Rao, M. R. Tetrahedron 1997, 53, 3457-3466.
37. Cironi, P.; Cuevas, C.; Albericio, F.; Álvarez, M. Tetrahedron 2004, 60, 8669-8676.
38. Cironi, P.; Manzanares, I.; Albericio, F.; Álvarez, M. Org. Lett. 2003, 5, 2959-2962.