Sequential intramolecular cyclobutadiene cycloaddition, ring-opening metathesis, and cope rearrangement: Total syntheses of (+)- and (-)-asteriscanolide [1]

Journal of the American Chemical Society

Volumn 122, Issue 33, 2000, Pages 8071-8072

  Limanto, John ^a   Snapper, Marc L ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; CYCLOBUTANE DERIVATIVE;

CHEMICAL MODIFICATION; CHEMICAL REACTION; LETTER; MOLECULAR DYNAMICS; SYNTHESIS;

EID: 0034706015     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001946b     Document Type: Letter

References (45)

1. (a) Tallarico, J. A.; Randall, M. L.; Snapper, M. L. J. Am. Chem. Soc. 1996, 118, 9196-9197.
2. (b) Limanto, J.; Snapper, M. L. J. Org. Chem. 1998, 63, 6440-6441.
3. (a) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611.
4. (b) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479.
5. (c) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157-7158.
6. (d) Tallarico, J. A.; Randall, M. L.; Snapper, M. L. Tetrahedron 1997, 53, 16511-16520.
7. (e) Schneider, M. F.; Blechen, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 411-412.
8. (f) Cuny, G. D.; Cao, J.; Hauske, J. R. Tetrahedron Lett. 1997, 38, 5237-5240.
9. (g) Cuny, G. D.; Hauske, J. R. CHEMTECH 1998, 28, 25-31.
10. (h) Randall, M. L.; Snapper, M. L. J. Mol. Catal. 1998, 133, 29-40.
11. San Feliciano, A.; Barrero, A. F.; Medarde, M.; Miguel del Corral, J. M.; Aramburu, A.; Perales, A.; Fayos, J. Tetrahedron Lett. 1985, 26, 2369-2372.
12. (a) Sarkar, T. K.; Gangopadhyay, P.; Binay, K.; Nandy, S. K.; Fang, J.-M. Tetrahedron Lett. 1998, 39, 8365-8366.
13. (b) Liu, S.; Crowe, W. E.; ACS 216th National Meeting Abstracts, American Chemical Society, Washington, DC, 1998; ORGN-235.
14. (c) Booker-Milburn, K. I.; Cowell, J. K.; Harris, L. J. Tetrahedron 1997, 53, 12319-12338.
15. (d) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361.
16. (e) Booker-Milburn, K. I.; Cowell, J. K. Tetrahedron Lett. 1996, 37, 2177-2180.
17. (f) Juliano, C. A. Thesis Dissertation, Florida State University, 1994.
18. (g) Booker-Milburn, K. I.; Cowell, J. K.; Harris, L. J. Tetrahedron Lett. 1994, 35, 3883-3886.
19. (h) Meister, P. G. Thesis Dissertation, Ohio State University 1991.
20. For recent reviews on the synthesis of cyclooctanoids, see: (i) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (j) Molander, G. A. Acc. Chem. Res. 1998, 31, 603-609.
21. For recent reviews on the synthesis of cyclooctanoids, see: (i) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881- 930. (j) Molander, G. A. Acc. Chem. Res. 1998, 31, 603-609.
22. (a) Cheung, Y. Y.; Krafft, M. E.; Juliano-Capucao, C. A. ACS 216th National Meeting Abstracts, American Chemical Society, Washington, DC. 1998; ORGN-238.
23. (b) Paquette, L. A.; Tae, J.; Arlington, M. P.; Sadoun, A. H. J. Am. Chem. Soc. 2000, 122, 2742-2748.
24. (c) Krafft, M. E.; Juliano-Capucao, C. A. Synthesis 2000, 0000.
25. (a) Wender, P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988. 110, 5904-5906.
26. (b) Ihle, N. C. Thesis Dissertation, Stanford University, 1989.
27. (a) Yoshihiko, I.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011-1013.
28. (b) Larock, R. C.; Hightower, T. R.; Kraus, G. A.; Hahn, P.; Zeng D. Tetrahedron Lett. 1995, 36, 2423-2426.
29. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553.
30. (b) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. Engl. 1988, 37, 1986-2012.
31. (c) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784.
32. Enantiomeric excess of 7 was determined by gas chromatography analysis on Supelco's Alpha Dex 120 fused silica capillary column.
33. Agar, J.; Kaplan, F.; Roberts, B. W. J. Org. Chem. 1974, 39, 3451-3452.
34. For an alternative preparation of complex 11, see: Bunz, U. Organometallics 1993, 12, 3594-3597.
35. For a similar reaction with ferrocene, see: Lednicer, D.; Hauser, C. R. Organic Syntheses; Wiley & Sons, New York, 1973; Collect. Vol. 5, pp 434-436.
36. (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
37. (b) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751-1753 and references therein.
38. For references to related ruthenium catalysts, see: (c) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207 and references therein.
39. (a) Bonadies, F.; Di Fabio, R. J. Org. Chem. 1984, 49, 1647-1649.
40. (b) Bonadies, F.; Bonini, C. Synth. Commun. 1988, 18, 1573-1580.
41. Spectrographic and physical properties of the compound generated were identical to previously reported data.
42. Semmelhack, M. F.; Stauffer, R. D.; Yamashita, A. J. Org. Chem. 1977, 42, 3180.
43. (a) Rao, V. V. R.; Devaprabhakara, D.; Chandrasekaran, S. J. Organomet. Chem. 1978, 162, C9.
44. (b) Lansbury, P. T.; Nickson, T. E. Tetrahedron Lett. 1982, 23, 2627.
45. (c) Piancatelli, G.; Scettri, A.; D'Auria, M. Synthesis 1982, 245.