Total synthesis of (+)-korupensamine B via an atropselective intermolecular biaryl coupling

Journal of the American Chemical Society

Volumn 132, Issue 40, 2010, Pages 14021-14023

  Huang, Shenlin ^a   Petersen, Tue B ^a   Lipshutz, Bruce H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC TOTAL SYNTHESIS; DIASTEREOSELECTIVE; STEREOCONTROL; SUZUKI-MIYAURA COUPLING; TETRAHYDROISOQUINOLINES; TOTAL SYNTHESIS;

CHEMICAL REACTIONS;

ISOQUINOLINE ALKALOID; KORUPENSAMINE B; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUZUKI REACTION;

ISOQUINOLINES; NAPHTHALENES; STEREOISOMERISM;

EID: 77957715450     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1065202     Document Type: Article

References (40)

1. Manfredi, K. P., Blunt, J. W., Cardellina, J. H., II, McMahon, J. B., Pannell, L. L., and Cragg, G. M. J. Med. Chem. 1991, 34, 3402-3405
2. Boyd, M. R., Hallock, Y. F., Cardellina, J. H., II, Manfredi, K. P., Blunt, J. W., McMahon, J. B., Buckheit, R. W., Bringmann, G., Schaffer, M., Cragg, G. M., Thomas, D. W., and Jato, J. G. J. Med. Chem. 1994, 37, 1740-1745
3. Hallock, Y. F., Manfredi, K. P., Dai, J. R., Cardellina, J. H., II, Gulakowski, R. J., McMahon, J. B., Schaffer, M., Stahl, M., Gulden, K. P., Bringmann, G., Francois, G., and Boyd, M. R. J. Nat. Prod. 1997, 60, 677-683
4. Bringmann, G. and Pokorny, F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1995; Vol. 46, pp 127 - 271.
5. Hallock, Y. F., Manfredi, K. P., Blunt, J. W., Cardellina, J. H., II, Schäffer, M., Gulden, K.-P., Bringmann, G., Lee, A. Y., Clardy, J., François, G., and Boyd, M. R. J. Org. Chem. 1994, 59, 6349-6355
6. Bringmann, G., Gulden, K.-P., Hallock, Y. F., Manfredi, K. P., Cardellina, J. H., II, Boyd, M. R., Kramer, B., and Fleischhauer, J. Tetrahedron 1994, 50, 7807-7814
7. Bringmann, G., Götz, R., Harmsen, S., Holenz, J., and Walter, R. Liebigs Ann. 1996, 2045-2058
8. Schlauer, J., Rückert, M., Wiesen, B., Herderich, M., Aké Assi, L., Haller, R. D., Bär, S., Fröhlich, K.-U., and Bringmann, G. Arch. Biochem. Biophys. 1998, 350, 87-94
9. For syntheses, see: Bringmann, G., Götz, R., Keller, P. A., Walter, R., Henschel, P., Schaffer, M., Stablein, M., Kelly, T. R., and Boyd, M. R. Heterocycles 1994, 39, 503-508
10. Bringmann, G. and Ochse, M. Synlett 1998, 1294-1296
11. Bringmann, G., Ochse, M., and Götz, R. J. Org. Chem. 2000, 65, 2069-2077
12. Watanabe, T., Shakadou, M., and Uemura, M. Synlett 2000, 1141-1144
13. Watanabe, T., Tanaka, Y., Shoda, R., Sakamoto, R., Kamikawa, K., and Uemura, M. J. Org. Chem. 2004, 69, 4152-4158
14. Hoye, T. R. and Chen, M. J. Org. Chem. 1996, 61, 7940-7942
15. Hoye, T. R. and Chen, M. Tetrahedron Lett. 1996, 37, 3099-3100
16. Hoye, T. R. and Chen, M. Tetrahedron Lett. 1996, 37, 3097-3098
17. Hoye, T. R., Chen, M., Hoang, B., Mi, L., and Priest, O. P. J. Org. Chem. 1999, 64, 7184-7201 For reviews, see: Bringmann, G., Breuning, M., and Tasler, S. Synthesis 1999, 525-558
18. Kamikawa, K. and Uemura, M. Synlett 2000, 938-949
19. Hassan, J., Sévignon, M., Gozzi, C., Schulz, E., and Lemaire, M. Chem. Rev. 2002, 102, 1359-1469
20. Baudoin, O. Eur. J. Org. Chem. 2005, 4223-4229
21. Bringmann, G., Mortimer, A. J. P., Keller, P. A., Gresser, M. J., Garner, J., and Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384-5427
22. Wallace, T. W. Org. Biomol. Chem. 2006, 4, 3197-3210
23. Bringmann, G., Gulder, T., and Gulder, T. A. M. In Asymmetric Synthesis: The Essentials; Christmann, M. and Bräse, S., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 246 - 250.
24. Lipshutz, B. H. and Keith, J. M. Angew. Chem. 1999, 111, 3743 - 3746
25. Angew. Chem., Int. Ed. 1999, 38, 3530 - 3533.
26. For reviews, see: Jones, G. B. and Chapman, B. J. Synthesis 1995, 475-497
27. Jones, G. B. Tetrahedron 2001, 57, 7999-8016
28. Bringmann, G., Hamm, A., and Schraut, M. Org. Lett. 2003, 5, 2805-2808
29. Lainé, D., Fujita, M., and Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1999, 1639-1645
30. Mitsunobu, O. Synthesis 1981, 1-28
31. Hughes, D. Org. React. 1992, 42, 335-395
32. Bischler, A. and Napieralski, B. Ber. Dtsch. Chem. Ges. 1893, 26, 1903-1908
33. The choice of base is crucial. A very low yield of the desired dihydroisoquinoline was obtained using 2,6-lutidine as the base.
34. The diastereomers can be separated by chromatography in most cases, and the stereochemistry can be assigned by saponification to the reported compound. See the Supporting Information. Also see ref 5.
35. Barder, T. E., Walker, S. D., Martinelli, J. R., and Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685-4696
36. 2/SPhos as the catalyst, but only traces of coupling product were observed in each case.
37. Bringmann, G. and Schneider, S. Synthesis 1983, 139-141
38. KOAc was added to avoid partial debenzylation.
39. Brosius, A. D., Overman, L. E., and Schwink, L. J. Am. Chem. Soc. 1999, 121, 700-709
40. The structure of tribenzylated korupensamine B (22) was confirmed by transformation into the known tetrabenzylated korupensamine B: Hobbs, P. D., Upender, V., and Dawson, M. I. Synlett 1997, 965-967