Unexpected dramatic substituent effect for tuning the selectivity in the double ring-closing metathesis reaction of N-containing tetraenes. An efficient synthesis of bicyclic izidine alkaloid skeletons

Organic Letters

Volumn 4, Issue 4, 2002, Pages 639-641

  Ma, Shengming ^a   Ni, Bukuo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

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ARTICLE;

EID: 0000218515     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0172673     Document Type: Article

References (30)

1. Ma, S.; Xu, B. J. Org. Chem. 1998, 63, 9156-9157.
2. (b) Ma, S.; Xu, B.; Ni, B. J. Org. Chem. 2000, 65, 8532-8543.
3. Wróbel, J. T. In The Alkaoids; Brossi, A., Ed.; Academic Press: San Diego, 1985; Vol. 26, pp 327-384.
4. (b) Numata, A.; Ibuka, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1987; Vol. 31, pp 193-315.
5. (c) Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 43, pp 185-288;
6. (d) Alkaliods: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1997; Vol. 5.
7. Michael, J. P. Nat. Prod. Rep. 1997, 14, 21-41.
8. (b) Michael, J. P. Nat. Prod. Rep. 1994, 11, 639-657.
9. (c) Liddell, J. R. Nat. Prod. Rep. 1997, 14, 653-660.
10. (d) Fuji, K.; Yamada, T.; Fujita, E.; Murata, H. Chem. Phar. Bull. 1978, 26, 515-2521.
11. (e) Jain, P.; Garraffo, H. M.; Yeh, H. J. C.; Spande, T. F.; Daly, J. W. J. Nat. Prod. 1996, 59, 1174-1178.
12. Pearson, W. H.; Suga, H. J. Org. Chem. 1998, 63, 9910-9918.
13. (b) Michel, P.; Rassat, A. J. Chem. Soc., Chem. Commun. 1999, 2281-2282.
14. (c) Takahata, H.; Kubota, M.; Ihara, K.; Okamoto, N.; Momose, T.; Azer, N.; Eldefrawi, A. T.; Eldefrawi, M. E. Tetrahedron: Asymmetry 1998, 9, 3289-3301.
15. (d) Comins, D. L.; Lamunyon, D. H. J. Org. Chem. 1992, 57, 5807-5809.
16. Alkene Metathesis in Organic Synthesis; Topics in Organometallic Chemistry; Fürstner, A., Ed.; Springer: Germany, 1998. For an account on Ru complex-catalyzed RCM reaction, see: Grubbs, R. H.; Miller, S.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. For a seminal paper of Rucatalyzed double RCM reaction, see: Fu, G. C.; Nguyen, S. B. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
17. Alkene Metathesis in Organic Synthesis; Topics in Organometallic Chemistry; Fürstner, A., Ed.; Springer: Germany, 1998. For an account on Ru complex-catalyzed RCM reaction, see: Grubbs, R. H.; Miller, S.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. For a seminal paper of Rucatalyzed double RCM reaction, see: Fu, G. C.; Nguyen, S. B. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
18. Alkene Metathesis in Organic Synthesis; Topics in Organometallic Chemistry; Fürstner, A., Ed.; Springer: Germany, 1998. For an account on Ru complex-catalyzed RCM reaction, see: Grubbs, R. H.; Miller, S.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. For a seminal paper of Rucatalyzed double RCM reaction, see: Fu, G. C.; Nguyen, S. B. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
19. For reports on the synthesis of izidine alkaloid skeletons through the ring by ring approach via a RCM reaction, see: (a) Paolucci, C.; Musiani, L.; Venturelli, F., Fava, A. Synthesis 1997, 1415-1417.
20. (b) Arisawa, M.; Takezawa, E.; Nishida, A.; Mori, M.; Nakagawa, M. Synlett 1997, 1179-1180.
21. (c) Barrett, A. G. M.; Baugh, S. P. D.; Gibson, V. C.; Giles, M. R.; Marshall, E. L.; Procopiou, P. A. J. Chem. Soc., Chem. Commun. 1997, 155-156.
22. For the formation of spirocyclic compounds via double or triple RCM, see: (a) Baylon, C.; Heck, M. P.; Mioskowski, C. J. Org. Chem. 1999, 64, 3354-3360.
23. (b) Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247-3250;
24. (c) Wallace, D. J.; Cowden, C. J.; Kennedy, D. J.; Ashwood, M. S.; Cottrell, I. F.; Dolling, U. H. Tetrahedron Lett. 2000, 41, 2027-2029.
25. (d) Heck, M. P.; Baylon, C.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2001, 3, 1989-1991.
26. For the formation of fused carbobicyclic or polycyclic compounds via double RCM reaction, see:(a) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. 1999, 38, 129-131.
27. (b) Clark, J. S.; Hamelin, O. Angew. Chem., Int. Ed. 2000, 39, 372-374.
28. As a typical example, 1c was prepared according to the following scheme: (equation presented)
29. int = 0.1721), no observation [I > 2σ(I)] 1658, parameters 163.
30. For a study on the relative reaction rate of olefin substrates with Ru carbenes see: Ulman, M.; Grubbs, R. H. Organometallics 1998, 17, 2484-2489.