Efficient Synthesis of dl-Zizaene Sesquiterpenes via Tandem Radical Cyclizations of N-Aziridinylimines

Synlett

Volumn 1997, Issue 8, 1997, Pages 947-949

  Kim, Sunggak ^a   Cheong, Jae Ho ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001352930     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-964     Document Type: Article

References (34)

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7. For selected examples, see: (a) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448. (b) Curran, D. P.; Kuo, S. C. J. Am. Chem. Soc. 1986, 108, 1106. (c) Iyoda, M.; Kushida, T.; Kitami, S.; Oda, M. J. Chem. Soc., Chem. Commun. 1987, 1607. (d) Jasperse, C. P.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 5601. (e) Clive, D. L. J.; Magnuson, S. R. Tetrahedron Lett. 1995, 36, 15. (f) Chen, Y-J.; Chang, W-H. J. Org. Chem. 1996, 61, 2536.
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9. For selected examples, see: (a) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448. (b) Curran, D. P.; Kuo, S. C. J. Am. Chem. Soc. 1986, 108, 1106. (c) Iyoda, M.; Kushida, T.; Kitami, S.; Oda, M. J. Chem. Soc., Chem. Commun. 1987, 1607. (d) Jasperse, C. P.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 5601. (e) Clive, D. L. J.; Magnuson, S. R. Tetrahedron Lett. 1995, 36, 15. (f) Chen, Y-J.; Chang, W-H. J. Org. Chem. 1996, 61, 2536.
10. For selected examples, see: (a) Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc. 1985, 107, 1448. (b) Curran, D. P.; Kuo, S. C. J. Am. Chem. Soc. 1986, 108, 1106. (c) Iyoda, M.; Kushida, T.; Kitami, S.; Oda, M. J. Chem. Soc., Chem. Commun. 1987, 1607. (d) Jasperse, C. P.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 5601. (e) Clive, D. L. J.; Magnuson, S. R. Tetrahedron Lett. 1995, 36, 15. (f) Chen, Y-J.; Chang, W-H. J. Org. Chem. 1996, 61, 2536.
11. (a) Kim, S.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882.
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14. For reviews, see: (a) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
15. Lee, H-Y.; Kim, D-I.; Kim, S. J. Chem. Soc., Chem. Commun. 1996, 1539.
16. 1H NMR.
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22. Other synthetic approaches, see: (a) Srikrishna, A.; Reddy, T. J. J. Org. Chem. 1996, 61, 6422. (b) Selvakumar, N.; Subba Rao, G. S. R. J. Chem. Soc. Perkin Trans. 1 1994, 3217. (c) Oppolzer, W.; Pitteloud, R.; Bernardinelli, G.; Baettig, K. Tetrahedron Lett. 1983, 24, 4975. (d) Hoffmann, H. M. R.; Henning, R.; Lalko, O. R. Angew. Chem., Int. Ed. Engl. 1982, 21, 442. (e) Liu, H.; Chan, W. H. Can. J. Chem. 1982, 60, 1081.
23. Other synthetic approaches, see: (a) Srikrishna, A.; Reddy, T. J. J. Org. Chem. 1996, 61, 6422. (b) Selvakumar, N.; Subba Rao, G. S. R. J. Chem. Soc. Perkin Trans. 1 1994, 3217. (c) Oppolzer, W.; Pitteloud, R.; Bernardinelli, G.; Baettig, K. Tetrahedron Lett. 1983, 24, 4975. (d) Hoffmann, H. M. R.; Henning, R.; Lalko, O. R. Angew. Chem., Int. Ed. Engl. 1982, 21, 442. (e) Liu, H.; Chan, W. H. Can. J. Chem. 1982, 60, 1081.
24. Other synthetic approaches, see: (a) Srikrishna, A.; Reddy, T. J. J. Org. Chem. 1996, 61, 6422. (b) Selvakumar, N.; Subba Rao, G. S. R. J. Chem. Soc. Perkin Trans. 1 1994, 3217. (c) Oppolzer, W.; Pitteloud, R.; Bernardinelli, G.; Baettig, K. Tetrahedron Lett. 1983, 24, 4975. (d) Hoffmann, H. M. R.; Henning, R.; Lalko, O. R. Angew. Chem., Int. Ed. Engl. 1982, 21, 442. (e) Liu, H.; Chan, W. H. Can. J. Chem. 1982, 60, 1081.
25. Other synthetic approaches, see: (a) Srikrishna, A.; Reddy, T. J. J. Org. Chem. 1996, 61, 6422. (b) Selvakumar, N.; Subba Rao, G. S. R. J. Chem. Soc. Perkin Trans. 1 1994, 3217. (c) Oppolzer, W.; Pitteloud, R.; Bernardinelli, G.; Baettig, K. Tetrahedron Lett. 1983, 24, 4975. (d) Hoffmann, H. M. R.; Henning, R.; Lalko, O. R. Angew. Chem., Int. Ed. Engl. 1982, 21, 442. (e) Liu, H.; Chan, W. H. Can. J. Chem. 1982, 60, 1081.
26. Other synthetic approaches, see: (a) Srikrishna, A.; Reddy, T. J. J. Org. Chem. 1996, 61, 6422. (b) Selvakumar, N.; Subba Rao, G. S. R. J. Chem. Soc. Perkin Trans. 1 1994, 3217. (c) Oppolzer, W.; Pitteloud, R.; Bernardinelli, G.; Baettig, K. Tetrahedron Lett. 1983, 24, 4975. (d) Hoffmann, H. M. R.; Henning, R.; Lalko, O. R. Angew. Chem., Int. Ed. Engl. 1982, 21, 442. (e) Liu, H.; Chan, W. H. Can. J. Chem. 1982, 60, 1081.
27. For the formation of tricyclic compounds using radical cyclizations, see: (a) Destabe, C.; Kilburn, J. D.; Knight, J. Tetrahedron Lett. 1993, 34, 3151. (b) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1994, 35, 8863. (c) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365.
28. For the formation of tricyclic compounds using radical cyclizations, see: (a) Destabe, C.; Kilburn, J. D.; Knight, J. Tetrahedron Lett. 1993, 34, 3151. (b) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1994, 35, 8863. (c) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365.
29. For the formation of tricyclic compounds using radical cyclizations, see: (a) Destabe, C.; Kilburn, J. D.; Knight, J. Tetrahedron Lett. 1993, 34, 3151. (b) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1994, 35, 8863. (c) Santagostino, M.; Kilburn, J. D. Tetrahedron Lett. 1995, 36, 1365.
30. Kim, S.; Jon, K. J. submitted to Bull. Korean Chem. Soc.
31. 3SnH and AIBN was dropwise added to the refluxing benzene solution of 17 for 30 h by a syringe pump. After being stirred for additional 2 h, the reaction mixture was concentrated and purified by silica gel column chromatography to give 18 (38 mg, 67%).
32. 22O : 206.1671, found 206.1672.
33. Deljac, A.; Mackay, W. D.; Pan, C. S. J.; Wiesner, K. J.; Wiesner, K. Can. J. Chem. 1972, 50, 726.
34. Buchi, G.; Hauser, A.; Limacher, J. J. Org. Chem. 1977, 42, 3323.