Diels-Alder reactions of oroidin and model compounds

Organic Letters

Volumn 8, Issue 5, 2006, Pages 819-821

  Pöverlein, Christoph ^a   Breckle, Gregor ^a   Lindel, Thomas ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; OROIDIN; PYRROLE DERIVATIVE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SPONGE (PORIFERA); TEMPERATURE;

ALKALOIDS; ANIMALS; CYCLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PORIFERA; PYRROLES; TEMPERATURE;

EID: 33644957990     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0526219     Document Type: Article

References (26)

1. Al Mourabit, A.; Potier, P. Eur. J. Org. Chem. 2001, 237-243.
2. Reviews on the synthesis of the pyrrole-imidazole alkaloids: (a) Hoffmann, H.; Lindel, T. Synthesis 2003, 1753-1783.
3. (b) Jacquot, D. E. N.; Lindel, T. Curr. Org. Chem. 2005, 9, 1551-1565.
4. (a) Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Ohta, T.; Nozoe, S. Tetrahedron 1990, 46, 5579-5586.
5. (b) Keifer, P. A.; Schwartz, R. E.; Koker, M. E. S.; Hughes, R. G., Jr.; Rittschof, D.; Rinehart, K. L. J. Org. Chem. 1991, 56, 2965-2975.
6. (c) Assmann, M.; Köck, M. Z. Naturforsch., C: Biosci. 2002, 57, 157-160.
7. Baran, P. S.; O'Malley, D. P.; Zografos, A. L. Angew. Chem., Int. Ed. 2004, 43, 2674-2677.
8. Walters, M. A.; Lee, M. D. Tetrahedron Lett. 1994, 35, 8307-8310.
9. (a) Lovely, C. J.; Du, H.; Dias, H. V. R. Org. Lett. 2001, 3, 1319-1322.
10. (b) Lovely, C. J.; Du, H.; Dias, H. V. R. Heterocycles 2003, 50, 1-7.
11. (c) Lovely, C. J.; Du, H.; He, Y.; Dias, H. V. R. Org. Lett. 2004, 6, 735-738.
12. He, Y.; Chen, Y.; Wu, H.; Lovely, C. J. Org. Lett. 2003, 5, 3623-3626.
13. (a) Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535-1538.
14. (b) Dransfield, P. J.; Wang, S.; Dilley, A.; Romo, D. Org. Lett. 2005, 7, 1679-1682.
15. Deghati, P. Y. F.; Wanner, M. J.; Koomen, G. J. Tetrahedron Lett. 1998, 39, 4561-4564.
16. Kawasaki, I.; Sakaguchi, N.; Fukushima, N.; Fujioka, N.; Nikaido, F.; Yamashita, M.; Ohta, S. Tetrahedron Lett. 2002, 43, 4377-4380.
17. The amino component of the amide oroidin has been dimerized with concomitant oxidation: Olofson, A.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 1997, 62, 7918-7919.
18. Abou-Jneid, R.; Ghoulami, S.; Martin, M.-T.; Dau, E. T. H.; Travert, N.; Al-Mourabit, A. Org. Lett. 2004, 6, 3933-3936.
19. Breckle, G.; Polborn, K.; Lindel, T. Z. Naturforsch., B: Chem. Sci. 2003, 58, 451-456.
20. Hayashi, M.; Sai, H.; Horikawa, H. Heterocycles 1998, 48, 1331-1335. A discussion on the estimated energetics of the putative cyclization of 12 is included in the Supporting Information.
21. 2H (2:2:1).
22. Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Eur. J. Org. Chem. 2001, 439-455.
23. Fattorusso, E.; Taglialatela-Scafati, O. Tetrahedron Lett. 2000, 41, 9917-9922.
24. For a pioneer cyclization of dihydrooroidin, see: Foley, L. H.; Büchi, G. J. Am. Chem. Soc. 1982, 104, 1776-1777.
25. For an oxidative cyclization of oroidin in DMSO/TFA, see: Lindel, T.; Breckle, G.; Hochgürtel, M.; Volk, C.; Grube, A.; Köck, M. Tetrahedron Lett. 2004, 45, 8149-8152.
26. While this manuscript was under review, an alternative total synthesis of rac-cyclooroidin was published: Papeo, G.; Gómez-Zurita Frau, M. A.; Borghi, D.; Varasi, M. Tetrahedron Lett. 2005, 46, 8635-8638.