Synthesis of 1,9-dideoxy-pre-axinellamine

Angewandte Chemie - International Edition

Volumn 47, Issue 19, 2008, Pages 3578-3580

  Yamaguchi, Junichiro ^a   Seiple, Ian B ^a   Young, Ian S ^a   O'Malley, Daniel P ^a   Maue, Michael ^a   Baran, Phil S ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Alkaloids; Axinellamine; Cascade reactions; Palau'amine; Total synthesis

Indexed keywords

CHEMICAL REACTIONS; RAW MATERIALS; SYNTHESIS (CHEMICAL);

ALKALOIDS; AXINELLAMINE; CASCADE REACTIONS; PALAU'AMINE; TOTAL SYNTHESIS;

COMPLEXATION;

1,9 DIDEOXYPREAXINELLAMINE; 1,9-DIDEOXYPREAXINELLAMINE; ALKALOID; AXINELLAMINE; IMIDAZOLE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALKALOIDS; IMIDAZOLES; PYRROLES;

EID: 44049103760     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705913     Document Type: Article

References (26)

1. M. Köck, A. Grube, I. B. Seiple, P. S. Baran, Angew. Chem. 2007, 119, 6706-6714;
2. Angew. Chem. Int. Ed. 2007, 46, 6586-6594.
3. Massadine: S. Nishimura, S. Matsunaga, M. Shibazaki, K. Suzuki, K. Furihata, R. W. M. van Soest, N. Fusetani, Org. Lett. 2003, 5, 2255-2257;
4. massadine chloride: A. Grube, S. Immel, P. S. Baran, M. Köck, Angew. Chem. 2007, 119, 6842-6845;
5. Angew. Chem. Int. Ed. 2007, 46, 6721-6724.
6. For the dimeric massadines (stylissadines), see: A. Grube, M. Köck, Org. Lett. 2006, 8, 4675-4678.
7. S. Urban, P. de A. Leone, A. R. Carroll, G. A. Fechner, J. Smith, J. N. A. Hooper, R. J. Quinn, J. Org. Chem. 1999, 64, 731-735.
8. Original palau'amine structure: a) R. B. Kinnel, H.-P. Gehrken, P. J. Scheuer, J. Am. Chem. Soc. 1993, 115, 3376-3377;
9. b) R. B. Kinnel, H.-P. Gehrken, R. Swali, G. Skoropowski, P. J. Scheuer, J. Org. Chem. 1998, 63, 3281-3286;
10. revised structure: c) A. Grube, M. Köck, Angew. Chem. 2007, 119, 2372-2376;
11. Angew. Chem. Int. Ed. 2007, 46, 2320-2324;
12. d) M. S. Buchanan, A. R. Carroll, R. Addepalli, V. M. Avery, J. N. A. Hooper, R. J. Quinn, J. Org. Chem. 2007, 72, 2309-2317;
13. e) H. Kobayashi, K. Kitamura, K. Nagai, Y. Nakao, N. Fusetani, R. W. M. van Soest, S. Matsunaga, Tetrahedron Lett. 2007, 48, 2127-2129.
14. For a summary ofapproa ches to the pyrrole-imidazole alkaloids, see reference [1] and references therein and the following recent reports: a) B. A. Lanman, L. E. Overman, R. Paulini, N. S. White, J. Am. Chem. Soc. 2007, 129, 12896-12900;
15. b) R. Sivappa, N. M. Hernandez, Y. He, C. J. Lovely, Org. Lett. 2007, 9, 3861-3864;
16. c) T. A. Cernak, J. L. Gleason, J. Org. Chem. 2008, 73, 702-710;
17. d) S. Wang, D. Romo, Angew. Chem. Int. Ed. 2008, 47, 1284-1286.
18. D. P. O'Malley, K. Li, M. Maue, A. L. Zografos, P. S. Baran, J. Am. Chem. Soc. 2007, 129, 4762-4775.
19. Prepared from the known aldehyde: P. Gosselin, C. Bourdy, S. Mille, A. Perrotin, J. Org. Chem. 1999, 64, 9557-9565.
20. T.-L. Ho in Tactics of Organic Synthesis, Wiley, New York, 1994, chap. 5, pp. 109-189.
21. J. L. Luche, J. Am. Chem. Soc. 1978, 100, 2226-2227.
22. Secured by ROESY analysis, see Supporting Information for details.
23. See following paper: D. P. O'Malley, J. Yamaguchi, I. S. Young, I. B. Seiple, P. S. Baran, Angew. Chem. 2008, 120, DOI: 10.1002/ ange.20081138;
24. Angew. Chem. Int. Ed. 2008, 47, DOI: 10.1002/ anie.20081138.
25. P. S. Baran, T. J. Maimone, J. M. Richter, Nature 2007, 446, 404-408.
26. See Supporting information for full characterization and copies ofspectra for all isolated intermediates. CCDC 680899 (8) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif..