Flexible strategy for the synthesis of pyrrolizidine alkaloids

Organic Letters

Volumn 10, Issue 16, 2008, Pages 3615-3618

  Donohoe, Timothy J ^a   Thomas, Rhian E ^a   Cheeseman, Matthew D ^a   Rigby, Caroline L ^a   Bhalay, Gurdip ^c   Linney, Ian D ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b James Black Foundation   (United Kingdom)

^c NOVARTIS HORSHAM RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; HYACINTHACINE A1; PYRROLIZIDINE ALKALOID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; STEREOISOMERISM; SYNTHESIS;

AMINES; HYDROXYLATION; MOLECULAR STRUCTURE; PYRROLIZIDINE ALKALOIDS; STEREOISOMERISM;

EID: 54049118080     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801415d     Document Type: Article

References (36)

1. Nash, R. J.; Fellows, L. E.; Dring, J. V.; Fleet, G. W. J; Derome, A. E.; Hamor, T. A.; Scofield, A. M.; Watkin, D. J. Tetrahedron Lett. 1988, 20, 2487.
2. (a) Robins, D. J. Nat. Prod. Rep. 1987, 4, 577.
3. (b) Chamberlin, A. R.; Chung, J. Y. L. J. Org. Chem. 1985, 50, 4425.
4. (a) Nash, R. J.; Thomas, P. I.; Waigh, R. D.; Fleet, G. W. J.; Wormald, M. R.; Lilley, P. M.; Watkin, D. J. Tetrahedron Lett. 1994, 35, 7849.
5. (b) Kato, A.; Kano, E.; Adachi, I.; Molyneux, R. J.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Wormald, M. R.; Kizu, H.; Ikeda, K.; Asano, N. Tetrahedron Asymmetry 2003, 14, 325.
6. (c) Yamashita, T; Yasuda, K.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Asano, N. J. Nat. Prod. 2002, 65, 1875.
7. (d) Kato, A.; Adachi, I.; Miyauchi, M.; Ikeda, K.; Komae, T.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Wormald, M. R.; Fleet, G. W. J.; Asano, N. Carbohydr. Res. 1999, 316, 95.
8. (e) Asano, N.; Kuroi, H.; Ikeda, K.; Kizu, H.; Kameda, Y.; Kato, A.; Adachi, I.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J. Tetrahedron Asymmetry 2000, 11, 1.
9. Asano, N. Glycobiology 2003, 13, 93R.
10. (a) Cox, T.; Lachmann, R.; Hollak, C.; Aerts, J.; van Weely, S.; Hrebicek, M.; Platt, F.; Butters, T.; Dwek, R.; Moyses, C.; Gow, I.; Elstein, D.; Zimran, A. Lancet 2000, 355, 1481.
11. (b) Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Praia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. Science 1997, 276, 428.
12. (a) Izquierdo, I.; Plaza, M. T.; Tamayo, J. A.; Sanchez-Cantlejo, F. Tetrahedron Asymmetry 2007, 18, 2211.
13. (b) Zhou, L.; Chen, J.; Cao, X. Synthesis 2007, 1359.
14. (c) Izquierdo, I.; Plaza, M. T.; Tamayo, J. A.; Rodriguez, M.; Martos, A. Tetrahedron 2006, 62, 6006.
15. (d) Tang, M.; Pyne, S. G. Tetrahedron 2004, 60, 5759.
16. (e) Tang, M.; Pyne, S. G. J. Org. Chem. 2003, 68, 7818.
17. (f) Tayoa, A.; Tamara, O.; Takagi, H.; Ishibashi, M. Synlett 2003, 35.
18. (g) Denmark, S. E.; Cottell, J. J. J. Org. Chem. 2001, 66, 4276.
19. (h) Ikota, N. Tetrahedron Lett. 1992, 33, 2553.
20. (i) Choi, S.; Bruce, I.; Fairbanks, A. J.; Fleet, G. W. J.; Jones, A. H.; Nash, R. J.; Fellows, L. E. Tetrahedron Lett. 1991, 32, 5517.
21. (a) Donohoe, T. J.; Rigby, C. L.; Thomas, R. E.; Nieuwenhuys, W. F.; Bhatti, F. L.; Cowley, A. R.; Bhalay, G.; Linney, I. D. J. Org. Chem. 2006, 71, 6298.
22. (b) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 5, 999.
23. 1H NMR spectrum: Poli, G Tetrahedron Lett. 1989, 30, 7385.
24. (a) Petrier, C.; Luche, J. L J. Org. Chem. 1985, 50, 910 For an example where these conditions gave the the Felkin-Ahn diastereomer with high selectivity,
25. see: (b) Nagaiah, K.; Sreenu, D.; Rao, S.; Yadav, J. S. Tetrahedron Lett. 2007, 48, 7173.
26. Nigam, S. C.; Mann, A.; Taddei, M.; Wermuth, C. G. Synth. Commun. 1989, 19, 3139.
27. (+)-2,3,7-Triepiaustraline was synthesised prior to its isolation as a natural product: Ikota, N.; Nakagawa, H.; Ohno, S.; Noguchi, K.; Okuyama, K Tetrahedron 1998, 54, 8985.
28. Tenaka, K.-I.; Maesoba, T.; Sawanishi, H. Heterocycles 2006, 68, 183.
29. 1 has previously been synthesized as the racemate by: (a) Donohoe, T. J.; Sintim, H. O.; Hollinshead, J. J. Org. Chem. 2005, 70, 7297.
30. It was synthesized asymmetrically by: (b) Chabaud, L.; Landais, Y.; Renaud, P. Org. Lett. 2005, 7, 2587.
31. (c) Izquierdo, I.; Plaza; Tamayo, J. A.; Sanchez-Cantalejo, F. Eur. J. Org. Chem. 2007, 6078.
32. The O-MIP protecting group proved too unstable to complete the synthesis.
33. 1H NMR spectrum.
34. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.
35. It has previously been observed that the synthetic samples of polyhydroxylated pyrrolizidines do not always match exactly the isolated NMR spectra depending on the method of purification, see: ref 13a. Wormald, M. R.; Nash, R. J.; Hrnciar, P.; White, J. D.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1998, 9, 2549.
36. 6 has been previously synthesised in an asymmetric manner, see ref 13c.