Synthesis of NP25302

Organic Letters

Volumn 13, Issue 22, 2011, Pages 5964-5967

  Stevens, Kiri ^a   Tyrrell, Andrew J ^a   Skerratt, Sarah ^b   Robertson, Jeremy ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

NP 25302; PYRROLIZIDINE ALKALOID; UREA; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CYCLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRROLIZIDINE ALKALOIDS; UREA; VINYL COMPOUNDS;

EID: 80955140306     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202381m     Document Type: Article

References (35)

1. Doyle, T. W.; Nettleton, D. E.; Balitz, D. M.; Moseley, J. E.; Grulich, R. E.; McCabe, T.; Clardy, J. J. Org. Chem. 1980, 45, 1324
2. Isolation and proposed structure: Hu, J.-F.; Wunderlich, D.; Thiericke, R.; Dahse, H.-M.; Grabley, S.; Feng, X.-Z.; Sattler, I. J. Antibiot. 2003, 56, 747
3. Structural reassignment: Snider, B. B.; Duvall, J. R.; Sattler, I.; Huang, X. Tetrahedron Lett. 2004, 45, 6725
4. Zhang, Q.; Schrader, K. K.; ElSohly, H. N.; Takamatsu, S. J. Antibiot. 2003, 56, 673
5. Bugni, T. S.; Woolery, M.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. J. Nat. Prod. 2006, 69, 1626
6. Contini, A.; Erba, E.; Trimarco, P. ARKIVOC 2008, (xii), 136.
7. Snider, B. B.; Duvall, J. R. Org. Lett. 2005, 7, 4519
8. Duvall, J. R.; Wu, F.; Snider, B. B. J. Org. Chem. 2006, 71, 8579
9. Volovenko, Y. M. Chem. Heterocycl. Compd. 1998, 33, 854
10. Katritzky, A. R.; Vincek, A. S.; Steel, P. J. Heterocycles 2008, 76, 1401
11. Tverdokhlebov, A. V.; Denisenko, A. V.; Tolmachev, A. A.; Volovenko, Y. M.; Shishkina, S. V.; Shishkin, O. V. Synthesis 2009, 1265
12. Nestorak, I. Y.; Tverdokhlebov, A. V.; Tolmachev, A. A.; Volovenko, Y. M. Heterocycles 2010, 81, 611
13. Heyns, K.; Vogelsang, G. Chem. Ber. 1954, 87, 1440
14. Cannon, W. N.; Jones, R. G. J. Org. Chem. 1957, 22, 1722
15. Boger, D. L.; Coleman, R. S. J. Org. Chem. 1986, 51, 3250
16. Boger, D. L.; Coleman, R. S. J. Am. Chem. Soc. 1987, 109, 2717
17. Smith, C. R.; Bunnelle, E. M.; Rhodes, A. J.; Sarpong, R. Org. Lett. 2007, 9, 1169
18. Yan, B.; Zhou, Y.; Zhang, H.; Chen, J.; Liu, Y. J. Org. Chem. 2007, 72, 7783
19. Bunnelle, E. M.; Smith, C. R.; Lee, S. K.; Singaram, S. W.; Rhodes, A. J.; Sarpong, R. Tetrahedron 2008, 64, 7008
20. Friel, D. K.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 9942
21. 5- Endo-dig N -cyclization onto alkynones: Gouault, N.; Le Roch, M.; Cornee, C.; David, M.; Uriac, P. J. Org. Chem. 2009, 74, 5614
22. Application in natural product synthesis [(+)-preussin from (S)-phenylalanine]: Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721
23. Turunen, B. J.; Georg, G. I. J. Am. Chem. Soc. 2006, 128, 8702
24. Ward, T. R.; Turunen, B. J.; Haack, T.; Neuenswander, B.; Shadrick, W.; Georg, G. I. Tetrahedron Lett. 2009, 50, 6494
25. Niphakis, M. J.; Georg, G. I. J. Org. Chem. 2010, 75, 6019
26. Niphakis, M. J.; Turunen, B. J.; Georg, G. I. J. Org. Chem. 2010, 75, 6793
27. Pepe, A.; Pamment, M.; Georg, G. I.; Malhotra, S. V. J. Org. Chem. 2011, 76, 3527
28. Beck, A. K.; Blank, S.; Job, K.; Seebach, D.; Sommerfeld, Th. Org. Synth. 1995, 72, 62
29. Tyrrell, A. J. D. Phil. Thesis, University of Oxford, Oxford, U.K., 2008.
30. Midland, M. M.; Tramontano, A.; Cable, J. R. J. Org. Chem. 1980, 45, 28
31. These conditions were found to be preferred in a related system: Reed, P. E.; Katzenellenbogen, J. A. J. Org. Chem. 1991, 56, 2624
32. Cf. Bastiaans, H. M. M.; van der Baan, J. L.; Ottenheijm, H. C. J. J. Org. Chem. 1997, 62, 3880
33. Shioiri, T.; Ninomiya, K.; Yamada, S.-i. J. Am. Chem. Soc. 1972, 94, 6203
34. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151
35. CCDC 834708 and 834707 contain crystallographic data for this paper (for compounds 29 ·HCl and 5 ·TFA, respectively). These can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.