A total synthesis of the marine alkaloid ningalin B from (S)-proline

Australian Journal of Chemistry

Volumn 62, Issue 7, 2009, Pages 683-691

  Hasse, Katrin ^a   Willis, Anthony C ^a   Banwell, Martin G ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

MARINE ALKALOIDS; N-ALKYLATION; OXIDATIVE BROMINATION; SUZUKI-MIYAURA CROSS-COUPLING; TOTAL SYNTHESIS;

HYDROCARBONS;

SYNTHESIS (CHEMICAL);

EID: 67949118730     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH09158     Document Type: Article

References (23)

1. H. Kang, W. Fenical, J. Org. Chem. 1997, 62, 3254. doi:10.1021/JO962132+
2. D. L. Boger, D. R. Soenen, C. W. Boyce, M. P. Hedrick, Q. Jin, J. Org. Chem. 2000, 65, 2479. doi:10.1021/JO9916535
3. For a recent and comprehensive review of this topic see: H. Fan, J. Peng, M. T. Hamann, J.-F. Hu, Chem. Rev. 2008, 108, 264. doi:10.1021/CR078199M
4. D. R. Soenen, I. Hwang, M. P. Hedrick, D. L. Boger, Bioorg. Med. Chem. Lett. 2003, 13, 1777. doi:10.1016/S0960-894X(03)00294-4
5. H. Tao, I. Hwang, D. L. Boger, Bioorg. Med. Chem. Lett. 2004, 14, 5979. doi:10.1016/J.BMCL.2004.10.002
6. M. Iwao, T. Takeuchi, N. Fujikawa, T. Fukuda, F. Ishibashi, Tetrahedron Lett. 2003, 44, 4443. doi:10.1016/S0040- 4039(03)01031-1
7. J. L. Bullington, R. R. Wolff, P. F. Jackson, J. Org. Chem. 2002, 67, 9439. doi:10.1021/JO026445I
8. J. T. Gupton, S. C. Clough, R. B. Miller, J. R. Lukens, C. A. Henry, R. P. F. Kanters, J. A. Sikorski, Tetrahedron 2003, 59, 207. doi:10.1016/S0040-4020(02)01475-8
9. C. Peschko, C. Winklhofer, A. Terpin, W. Steglich, Synthesis 2006, 3048.
10. (a) M. G. Banwell, B. L. Flynn, E. Hamel, D. C. R. Hockless, Chem. Commun. 1997, 207. doi:10.1039/A606793J
11. (b) M. Banwell, B. Flynn, D. Hockless, Chem. Commun. 1997, 2259. doi:10.1039/A705874H
12. (c) M. G. Banwell, A. M. Bray, A. C. Willis, D. J. Wong, New J. Chem. 1999, 23, 687. doi:10.1039/A903330K
13. (d) M. R. Heinrich, W. Steglich, M. G. Banwell, Y. Kashman, Tetrahedron 2003, 59, 9239. doi:10.1016/J.TET.2003.02.005
14. (e) D. M. Pinkerton, M. G. Banwell, A. C. Willis, Org. Lett. 2007, 9, 5127. doi:10.1021/OL7024313
15. L. C. Axford, K. E. Holden, K. Hasse, M. G. Banwell, W. Steglich, J. Wagler, A. C. Willis, Aust. J. Chem. 2008, 61, 80. doi:10.1071/CH07402
16. V. A. Burgess, C. J. Easton, M. P. Hay, J. Am. Chem. Soc. 1989, 111, 1047. doi:10.1021/JA00185A039
17. This compound was purchased from Boron Molecular Pty Ltd, Noble Park, VIC 3174, Australia (Available online at: http://www.boronmolecular.com; accessed 19 May 2009).
18. S. T. Handy, Y. Zhang, H. Bregman, J. Org. Chem. 2004, 69, 2362. doi:10.1021/JO0352833
19. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923. doi:10.1021/JO00408A041
20. A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518. doi:10.1021/OM9503712
21. DENZO-SMN. Z. Otwinowski W. Minor, in Methods in Enzymology, Volume 276: Macromolecular Crystallography, Part A (Eds C. W. Carter, Jr, R. M. Sweet) 1997, pp. 307-326 (Academic Press: NewYork, NY).
22. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Cryst. 1994, 27, 435. doi:10.1107/S002188989400021X
23. P. W. Betteridge, J. R. Carruthers, R. I. Cooper, K. Prout, D. J. Watkin, J. Appl. Cryst. 2003, 36, 1487. doi:10.1107/ S0021889803021800