A ring-rearrangement metathesis approach toward the synthesis of cyclopenta- and cyclohexa[c]indene systems

Organic Letters

Volumn 6, Issue 21, 2004, Pages 3719-3722

  Holtsclaw, Jeremy ^a   Koreeda, Masato ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DESOGESTREL;

ARTICLE; CATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; RING OPENING; SYNTHESIS;

EID: 7244244217     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048650l     Document Type: Article

References (45)

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16. For recent reviews, see: (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (d) Schrock, R. R. In Carbene Chemistry; Bertrand, G., Ed.; Marcel Dekker: New York, 2002; pp 205-230. (e) Grubbs, R. H.; Trnka, T. M.; Sanford, M. S. In Current Methods in Inorganic Chemistry; Kurokawa, H., Yamamoto, A., Eds.; Elsevier: Amsterdam, 2003; Vol. 3, pp 187-231. (f) Arjona, O.; Csáky, A. G.; Plumet, J. Eur. J. Org. Chem. 2003, 611-622. (g) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923. (h) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633. (i) Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8-23. (j) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. (k) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239-2258.
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18. For recent reviews, see: (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (d) Schrock, R. R. In Carbene Chemistry; Bertrand, G., Ed.; Marcel Dekker: New York, 2002; pp 205-230. (e) Grubbs, R. H.; Trnka, T. M.; Sanford, M. S. In Current Methods in Inorganic Chemistry; Kurokawa, H., Yamamoto, A., Eds.; Elsevier: Amsterdam, 2003; Vol. 3, pp 187-231. (f) Arjona, O.; Csáky, A. G.; Plumet, J. Eur. J. Org. Chem. 2003, 611-622. (g) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923. (h) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633. (i) Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8-23. (j) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. (k) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239-2258.
19. For recent reviews, see: (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (d) Schrock, R. R. In Carbene Chemistry; Bertrand, G., Ed.; Marcel Dekker: New York, 2002; pp 205-230. (e) Grubbs, R. H.; Trnka, T. M.; Sanford, M. S. In Current Methods in Inorganic Chemistry; Kurokawa, H., Yamamoto, A., Eds.; Elsevier: Amsterdam, 2003; Vol. 3, pp 187-231. (f) Arjona, O.; Csáky, A. G.; Plumet, J. Eur. J. Org. Chem. 2003, 611-622. (g) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923. (h) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633. (i) Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8-23. (j) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. (k) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239-2258.
20. For recent reviews, see: (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (d) Schrock, R. R. In Carbene Chemistry; Bertrand, G., Ed.; Marcel Dekker: New York, 2002; pp 205-230. (e) Grubbs, R. H.; Trnka, T. M.; Sanford, M. S. In Current Methods in Inorganic Chemistry; Kurokawa, H., Yamamoto, A., Eds.; Elsevier: Amsterdam, 2003; Vol. 3, pp 187-231. (f) Arjona, O.; Csáky, A. G.; Plumet, J. Eur. J. Org. Chem. 2003, 611-622. (g) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923. (h) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633. (i) Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8-23. (j) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. (k) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239-2258.
21. For recent reviews, see: (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (d) Schrock, R. R. In Carbene Chemistry; Bertrand, G., Ed.; Marcel Dekker: New York, 2002; pp 205-230. (e) Grubbs, R. H.; Trnka, T. M.; Sanford, M. S. In Current Methods in Inorganic Chemistry; Kurokawa, H., Yamamoto, A., Eds.; Elsevier: Amsterdam, 2003; Vol. 3, pp 187-231. (f) Arjona, O.; Csáky, A. G.; Plumet, J. Eur. J. Org. Chem. 2003, 611-622. (g) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923. (h) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633. (i) Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8-23. (j) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. (k) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239-2258.
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23. For recent reviews, see: (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29. (d) Schrock, R. R. In Carbene Chemistry; Bertrand, G., Ed.; Marcel Dekker: New York, 2002; pp 205-230. (e) Grubbs, R. H.; Trnka, T. M.; Sanford, M. S. In Current Methods in Inorganic Chemistry; Kurokawa, H., Yamamoto, A., Eds.; Elsevier: Amsterdam, 2003; Vol. 3, pp 187-231. (f) Arjona, O.; Csáky, A. G.; Plumet, J. Eur. J. Org. Chem. 2003, 611-622. (g) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923. (h) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633. (i) Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8-23. (j) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. (k) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239-2258.
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31. For some recent, select examples of the RCM reaction of norbornene compounds, see: (a) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259. (b) Stragies, R.; Blechert, S. Synlett 1998, 169-170. (c) Hagiwara, H.; Katsumi, T.; Endou, S.; Hoshi, T.; Suzuki, T. Tetrahedron 2002, 58, 6651-6654. (d) Tsang, W. C. P.; Jernelius, J. A.; Cortez, G. A.; Weatherhead, G. S.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 2591-2596.
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33. Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291-293.
34. (a) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543-6554.
35. (b) Hong, S. H.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2004, 126, 7414-7415.
36. Randl, S.; Blechert, S. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 2, pp 151-175.
37. A relayed RCM strategy is similar in its concept to what is described in this report but differs in that, in the former approach, the tether used does not end up in the product. See, for example: Wang, X.; Bowman, E. J.; Bowman, B. J.; Porco, J. A. Angew. Chem., Int. Ed. 2004, 43, 3601-3605 and references therein.
38. (a) Bly, R. K.; Bly, R. S. J. Org. Chem. 1963, 28, 3165-3172.
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44. Strain energy of norbornene is estimated to be 100 kJ/mol. (a) Lebedev, B.; Smirnova, N.; Kiparisova, Y.; Makovetsky, K. Makromol. Chem. 1992, 193, 1399-1411. (b) North, M. In Advances in Strained and Interesting Organic Molecules; Halton, B., Ed.; JAI Press: Stamford, CN, 2000; Vol. 8, pp 145-185.
45. Strain energy of norbornene is estimated to be 100 kJ/mol. (a) Lebedev, B.; Smirnova, N.; Kiparisova, Y.; Makovetsky, K. Makromol. Chem. 1992, 193, 1399-1411. (b) North, M. In Advances in Strained and Interesting Organic Molecules; Halton, B., Ed.; JAI Press: Stamford, CN, 2000; Vol. 8, pp 145-185.