Total synthesis of marine bisindole alkaloids, (+)-hamacanthins A, B and (-)-antipode of 0cis-dihydrohamacanthin B

Tetrahedron

Volumn 61, Issue 9, 2005, Pages 2309-2318

  Kouko, Takashi ^a   Matsumura, Ken ^a   Kawasaki, Tomomi ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Absolute configuration; Bromoindole; Indolylglycinol; Oxazolidin 2 one

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; DIHYDROHAMACANTHIN B; HAMACANTHIN A; HAMACANTHIN B; INDOLE ALKALOID; INDOLYLGLYCINOL; N (2 AMINOETHYL) 2 OXOETHANAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 13644263286     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.058     Document Type: Article

References (28)

1. S. Kohmoto, Y. Kashman, O.J. McConnell, K.L. Rinehart Jr., A. Wright, and F. Koehn J. Org. Chem. 53 1988 3116 3118
2. S.A. Morris, and R.J. Andersen Tetrahedron 46 1990 715 720
3. E. Fahy, B.C.M. Potts, D.J. Faulkner, and K. Smith J. Nat. Prod. 54 1991 564 569
4. A.E. Wright, S.A. Pomponi, S.S. Cross, and P. McCarthy J. Org. Chem. 57 1992 4772 4775
5. L.M. Murray, T.K. Lim, J.N.A. Hooper, and R.J. Capon Aust. J. Chem. 48 1995 2053 2058
6. R.J. Capon, F. Rooney, L.M. Murray, E. Collins, A.T.R. Sim, J.A.P. Rostas, M.S. Butler, and A.R. Carrol J. Nat. Prod. 61 1998 660 662
7. A. Cutignano, G. Bifulco, I. Bruno, A. Casapullo, L. Gomez-Paloma, and R. Riccio Tetrahedron 56 2000 3743 3748
8. S.P. Gunasekera, P.J. McCarthy, and M. Kelly-Borges J. Nat. Prod. 57 1994 1437 1441
9. A. Casapullo, G. Bifulco, I. Bruno, and R. Riccio J. Nat. Prod. 63 2000 447 451
10. Total synthesis of dragmacidins: (a) B. Jiang, J.M. Smallheer, C. Amaral-Ly, and M.A. Wuonola J. Org. Chem. 59 1994 6823 6827
11. C.R. Whitlock, and M.P. Cava Tetrahedron Lett. 35 1994 371 374
12. F.Y. Miyake, K. Yakushijin, and D.A. Horne Org. Lett. 2 2000 3185 3187
13. N.K. Garg, R. Sarpong, and B.M. Stoltz J. Am. Chem. Soc. 124 2002 13179 13184
14. N.K. Garg, D.D. Caspi, and B.M. Stoltz J. Am. Chem. Soc. 126 2004 9552 9553
15. Total synthesis of hamacanthins: (a) B. Jiang, C.-G. Yang, and J. Wang J. Org. Chem. 66 2001 4865 4869
16. B. Jiang, C.-G. Yang, and J. Wang J. Org. Chem. 67 2002 1396 1398
17. C.-G. Yang, J. Wang, X.-X. Tang, and B. Jiang Tetrahedron: Asymmetry 13 2002 383 394
18. F.Y. Miyake, K. Yakushijin, and D.A. Horne Org. Lett. 4 2002 941 943
19. T. Kawasaki, H. Enoki, K. Matsumura, M. Ohyama, M. Inagawa, and M. Sakamoto Org. Lett. 2 2000 3027 3029
20. T. Kawasaki, K. Ohno, H. Enoki, Y. Umemoto, and M. Sakamoto Tetrahedron Lett 43 2002 4245 4248
21. T. Kawasaki, T. Kouko, H. Totsuka, and K. Hiramatsu Tetrahedron Lett. 44 2003 8849 8852
22. T. Kouko, J. Kobayashi, A. Ohta, M. Sakamoto, and T. Kawasaki Synthesis 2004 2463 2470
23. T. Kawasaki, Y. Nonaka, K. Matsumura, M. Monai, and M. Sakamoto Synth. Commun. 29 1999 3251 3261
24. K. Lee, and J.K. Cha J. Am. Chem. Soc. 123 2001 5590 5591
25. 1H NMR spectrum.
26. Attempted separation of the E-, Z-mixture using column chromatography was unsuccessful.
27. M. Prashad, D. Har, H.-Y. Kim, and O. Repic Tetrahedron Lett. 39 1998 7067 7070 Since an inseparable mixture of 9 and its 1-acetyl derivative 12 was obtained, deacetylation was carried out in a one-pot procedure
28. The 2,5-pyrazinone 23 was treated with sodium cyanoborohydride to convert into trans- and cis-dihydrohamacanthins A (1c,d) as an inseparable mixture, whose ratio was ca. 1:1.