New stereoselective entry to azaspirocyclic nucleus of halichlorine and pinnaic acids by radical translocation/cyclization reaction

Organic Letters

Volumn 5, Issue 17, 2003, Pages 3017-3020

  Takasu, Kiyosei ^a   Ohsato, Hiroshi ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL COMPOUND; CHLORINE DERIVATIVE; PINNAIC ACID; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY;

ALKALOIDS; AZO COMPOUNDS; CYCLIZATION; FREE RADICALS; PIPERIDINES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 0141521414     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034942v     Document Type: Article

References (29)

1. Kuramoato, M.; Tong, C.; Yamada, K.; Chiba, T.; Hayashi, Y.; Uemura, D. Tetrahedron Lett. 1996, 37, 3867-3870.
2. Chou, T.; Kuramoto, M.; Otani, Y.; Shikano, M.; Yazawa, K.; Uemura, D. Tetrahedron Lett. 1996, 37, 3871-3874. The proposed structure in their report has been revised by Danishefsky's goup. See ref 3c.
3. (a) Trauner, D.; Schwarz, J. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1999, 38, 3542-3544.
4. (b) Carson, M. W.; Kim, G.; Hentemann, M. F.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4450-4452.
5. (c) Carson, M. W.; Kim, G.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4453-4456.
6. (d) Hayakawa, I.; Arimoto, H.; Uemura, D. Heterocycles 2003, 59, 441-444.
7. (a) Arimoto, H.; Asano, S.; Uemura, D. Tetrahedron Lett. 1999, 40, 3583-3586.
8. (b) Trauner, D. Danishefsky, S. J. Tetrahedron Lett. 1999, 40, 6513-6516.
9. (c) Lee, S.; Zhao, Z. Tetrahedron Lett. 1999, 40, 7921-7924.
10. (d) Clive, D. L.; Yeh, V. S. C. Tetrahedron Lett. 1999, 40, 8503-8507.
11. (e) Koviach, J. L.; Forsyth, C. J. Tetrahedron Lett. 1999, 40, 8529-8532.
12. (f) Shindo, M.; Fukuda, Y.; Shishido, K. Tetrahedron Lett. 2000, 41, 929-932.
13. (g) Wright, D. L.; Schulte, J. P., II; Page, M. A. Org. Lett. 2000, 2, 1847-1850.
14. (h) White, J. D.; Blakemore, P. R.; Korf, E. A.; Yokochi, A. F. T. Org. Lett. 2001, 3, 413-415.
15. For a review of radical translocation reactions, see: (a) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103. For examples of radical translocation/cyclization reaction in synthesis, see: (b) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896-898. (c) Curran, D. P.; Abraham, A. C.; Liu, H. J. Org. Chem. 1991, 56, 4337-4339. (d) Sha, C.-K.; Hsu, C.-W.; Chen, Y.-T.; Cheng, S.-Y. Tetrahedron Lett. 2000, 41, 9865-9869. (e) Sato, T.; Yamazaki, T.; Nakanishi, Y.; Uenishi, J.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 2002, 1438-1443. (f) Curran, D. P. ; Liu, H. J. Chem. Soc., Perkin Trans. 1 1994, 1377-1394.
16. For a review of radical translocation reactions, see: (a) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103. For examples of radical translocation/cyclization reaction in synthesis, see: (b) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896-898. (c) Curran, D. P.; Abraham, A. C.; Liu, H. J. Org. Chem. 1991, 56, 4337-4339. (d) Sha, C.-K.; Hsu, C.-W.; Chen, Y.-T.; Cheng, S.-Y. Tetrahedron Lett. 2000, 41, 9865-9869. (e) Sato, T.; Yamazaki, T.; Nakanishi, Y.; Uenishi, J.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 2002, 1438-1443. (f) Curran, D. P. ; Liu, H. J. Chem. Soc., Perkin Trans. 1 1994, 1377-1394.
17. For a review of radical translocation reactions, see: (a) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103. For examples of radical translocation/cyclization reaction in synthesis, see: (b) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896-898. (c) Curran, D. P.; Abraham, A. C.; Liu, H. J. Org. Chem. 1991, 56, 4337-4339. (d) Sha, C.-K.; Hsu, C.-W.; Chen, Y.-T.; Cheng, S.-Y. Tetrahedron Lett. 2000, 41, 9865-9869. (e) Sato, T.; Yamazaki, T.; Nakanishi, Y.; Uenishi, J.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 2002, 1438-1443. (f) Curran, D. P. ; Liu, H. J. Chem. Soc., Perkin Trans. 1 1994, 1377-1394.
18. For a review of radical translocation reactions, see: (a) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103. For examples of radical translocation/cyclization reaction in synthesis, see: (b) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896-898. (c) Curran, D. P.; Abraham, A. C.; Liu, H. J. Org. Chem. 1991, 56, 4337-4339. (d) Sha, C.-K.; Hsu, C.-W.; Chen, Y.-T.; Cheng, S.-Y. Tetrahedron Lett. 2000, 41, 9865-9869. (e) Sato, T.; Yamazaki, T.; Nakanishi, Y.; Uenishi, J.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 2002, 1438-1443. (f) Curran, D. P. ; Liu, H. J. Chem. Soc., Perkin Trans. 1 1994, 1377-1394.
19. For a review of radical translocation reactions, see: (a) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103. For examples of radical translocation/cyclization reaction in synthesis, see: (b) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896-898. (c) Curran, D. P.; Abraham, A. C.; Liu, H. J. Org. Chem. 1991, 56, 4337-4339. (d) Sha, C.-K.; Hsu, C.-W.; Chen, Y.-T.; Cheng, S.-Y. Tetrahedron Lett. 2000, 41, 9865-9869. (e) Sato, T.; Yamazaki, T.; Nakanishi, Y.; Uenishi, J.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 2002, 1438-1443. (f) Curran, D. P. ; Liu, H. J. Chem. Soc., Perkin Trans. 1 1994, 1377-1394.
20. For a review of radical translocation reactions, see: (a) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103. For examples of radical translocation/cyclization reaction in synthesis, see: (b) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896-898. (c) Curran, D. P.; Abraham, A. C.; Liu, H. J. Org. Chem. 1991, 56, 4337-4339. (d) Sha, C.-K.; Hsu, C.-W.; Chen, Y.-T.; Cheng, S.-Y. Tetrahedron Lett. 2000, 41, 9865-9869. (e) Sato, T.; Yamazaki, T.; Nakanishi, Y.; Uenishi, J.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 2002, 1438-1443. (f) Curran, D. P. ; Liu, H. J. Chem. Soc., Perkin Trans. 1 1994, 1377-1394.
21. Hart, D. J.; Tsai, Y.-M. J. Am. Chem. Soc. 1984, 106, 8209-8217.
22. Keen, S. P.; Weinreb, S. M. J. Org. Chem. 1998, 63, 6739-6741.
23. Ley, S. V.; Lygo, B.; Sternfield, F.; Wonnacott, A. Tetrahedron 1986, 42, 4333-4342.
24. Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784.
25. (a) Roth, M.; Dubs, P.; Götschi, E.; Eschenmoser, A. Helv. Chim. Acta 1971, 54, 710-734.
26. (b) Tanino, H.; Nakata, T.; Kaneko, T.; Kishi, Y. J. Am. Chem. Soc. 1977, 99, 2818-2819.
27. (a) Myers, A. G.; Yang, B. H.; Kopecky, D. J. Tetrahedron Lett. 1996, 37, 3623-3626.
28. (b) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592.
29. We have proven that a variety of heteroatom-containing spirocycles can be synthesized by our strategy. The efforts will be published elsewhere.