Formal synthesis of (±)-peduncularine: Use of the [3 + 2] annulation of allylic silanes and chlorosulfonyl isocyanate

Organic Letters

Volumn 2, Issue 5, 2000, Pages 621-622

  Roberson, Claudia W ^a   Woerpel, K A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000365479     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9913744     Document Type: Article

References (21)

1. Bick, I. R. C.; Bremner, J. B.; Preston, N. W. J. Chem. Soc., Chem. Commun. 1971, 1155-1156.
2. Ros, H.-P.; Kyburz, R.; Preston, N. W.; Gallagher, R. T.; Bick, I. R. C.; Hesse, M. Helv. Chim. Acta 1979, 62, 481-487.
3. Bick, I. R. C.; Hai, M. A. In The Alkaloids; Brossi, A., Ed.; Academic: New York, 1985; Vol. 24; pp 113-151.
4. For lead references on other 6-azabicyclo[3.2.1 ]octane systems, see: (a) Holmes, A. B.; Kee, A.; Ladduwahettey, T.; Smith, D. F. J. Chem. Soc., Chem. Commun. 1990, 1412-1414.
5. (b) Triggle, D. J.; Kwon, Y. W.; Abraham, P.; Pitner, J. B.; Mascarella, S. W., Carroll, F. I. J. Med. Chem. 1991, 34, 3164-3171.
6. Klaver, W. J.; Hiemstra, H.; Speckamp, W. N. J. Am. Chem. Soc. 1989, 111, 2588-2595.
7. Rigby, J. H.; Meyer, J. H. Synlett 1999, S1, 860-862.
8. Roberson, C. W.; Woerpel, K. A. J. Org. Chem. 1999, 64, 1434-1435.
9. Peng, Z.-H.; Woerpel, K. A. University of California, Irvine, unpublished results.
10. Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 17, 1295-1298.
11. Fleming, I.; Dunogués, J.; Smithers, R. Org. React. 1989, 37, 57-574.
12. Durst, T.; O'Sullivan, M. J. J. Org. Chem. 1970, 35, 2043-2044.
13. Kahn, S. D.; Pau, C. F.; Chamberlin, A. R.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 650-663.
14. Lambert, J. B.; Zhao, Y.; Emblidge, R. W.; Salvador, L. A.; Liu, X.; So, J.-H.; Chelius, E. C. Acc. Chem. Res. 1999, 32, 183-190.
15. Jarvie, A. W. P.; Holt, A.; Thompson, J. J. Chem. Soc. B 1969, 852-855.
16. Dubé, D.; Scholte, A. A. Tetrahedron Lett. 1999, 40, 2295-2298.
17. Groaning, M. D.; Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1998, 63, 5517-5522.
18. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
19. Jones, G.; Landais, Y. Tetrahedron 1996, 52, 7599-7662.
20. Fleming, I. Chemtracts-Org. Chem. 1996, 9, 1-64.
21. Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044-6046.