Remarkable selectivity in addition of alcohols to epoxydienes of 5,7 bicyclic and 5,7,6 tricyclic systems

Journal of Organic Chemistry

Volumn 70, Issue 3, 2005, Pages 1077-1080

  Boyer, François Didier ^a   Hanna, Issam ^b  

^a CEMAGREF   (France)

^b LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSIS; DERIVATIVES; OLEFINS;

EPOXYDIENES; OXIRANES;

ADDITION REACTIONS;

1,2 EPOXY 3 BUTENE; ALCOHOL; ALKADIENE; ALLYL ALCOHOL; EPOXIDE; LEWIS ACID;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CONJUGATION; DRUG STRUCTURE; MATHEMATICAL ANALYSIS; REACTION ANALYSIS; RING CLOSING METATHESIS; SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 13244264844     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0481295     Document Type: Article

References (40)

1. Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5; p 931.
2. N2′ addition of dithiane anions to vinyl epoxides, see: Smith, A. B.; Pitram, S. M.; Boldi, A. M.; Gaunt, M. J.; Sfouggatakis, C.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 14435.
3. N2′ addition of organocuprates to vinyl epoxides, see: Marshall, J. A. Chem. Rev. 1989, 89, 1503.
4. N2′ addition of organocuprates to vinyl epoxides, see: Marshall, J. A. Chem. Rev. 1989, 89, 1503.
5. N2′ addition of organocuprates to vinyl epoxides, see: Marshall, J. A. Chem. Rev. 1989, 89, 1503.
6. N2′ palladium-catalyzed addition of alkoxides, see: (a) Deardorff, D. R.; Myles, D. C.; MacFerrin, K. D. Tetrahedron Lett. 1985, 26, 5615. (b) Deardorff, D. R.; Myles, D. C. Organic Synthesis; Wiley & Sons: New York, 1993; Collect. Vol. 8, p 13. (c) Trost, B. M.; Ito, N.; Greenspan, P. D. Tetrahedron Lett. 1993, 34, 1421. (d) Snider, B. B.; Hawryluk, N. A. Org. Lett. 2001, 3, 569.
7. N2′ palladium-catalyzed addition of alkoxides, see: (a) Deardorff, D. R.; Myles, D. C.; MacFerrin, K. D. Tetrahedron Lett. 1985, 26, 5615. (b) Deardorff, D. R.; Myles, D. C. Organic Synthesis; Wiley & Sons: New York, 1993; Collect. Vol. 8, p 13. (c) Trost, B. M.; Ito, N.; Greenspan, P. D. Tetrahedron Lett. 1993, 34, 1421. (d) Snider, B. B.; Hawryluk, N. A. Org. Lett. 2001, 3, 569.
8. N2′ palladium-catalyzed addition of alkoxides, see: (a) Deardorff, D. R.; Myles, D. C.; MacFerrin, K. D. Tetrahedron Lett. 1985, 26, 5615. (b) Deardorff, D. R.; Myles, D. C. Organic Synthesis; Wiley & Sons: New York, 1993; Collect. Vol. 8, p 13. (c) Trost, B. M.; Ito, N.; Greenspan, P. D. Tetrahedron Lett. 1993, 34, 1421. (d) Snider, B. B.; Hawryluk, N. A. Org. Lett. 2001, 3, 569.
9. N2′ palladium-catalyzed addition of alkoxides, see: (a) Deardorff, D. R.; Myles, D. C.; MacFerrin, K. D. Tetrahedron Lett. 1985, 26, 5615. (b) Deardorff, D. R.; Myles, D. C. Organic Synthesis; Wiley & Sons: New York, 1993; Collect. Vol. 8, p 13. (c) Trost, B. M.; Ito, N.; Greenspan, P. D. Tetrahedron Lett. 1993, 34, 1421. (d) Snider, B. B.; Hawryluk, N. A. Org. Lett. 2001, 3, 569.
10. N2 addition of alkyllithiums, see: Alexakis, A.; Vranken, E.; Mangenay, P.; Chemla, F. J. Chem. Soc., Perkin Trans. 1 2000, 3352.
11. (b) For 1,2-addition of alcohols, see: Prestat, G.; Baylon, C.; Heck, M.-P.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 3829.
12. For rhodium-catalyzed 1,2-ring opening of vinyl epoxides, see: Fagnou, K.; Lautens, M. Org. Lett. 2000, 2, 2319.
13. Boyer, F.-D.; Hanna, I.; Ricard, L. Org. Lett. 2004, 6, 1817.
14. Isolation and biological activity: (a) Brady, S. F.; Singh, M. P.; Janso, J. E.; Clardy, J. J. Am. Chem. Soc. 2000, 122, 2116. (b) Brady, S. F.; Bondi, S. M.; Clardy, J. J. Am. Chem. Soc. 2001, 123, 9900. (c) Singh, M. P.; Janso, J. E.; Luckman, S. W.; Brady, S. F.; Clardy, J.; Greenstein, M.; Maiese, W. M. J. Antibiot. 2000, 53, 256.
15. Isolation and biological activity: (a) Brady, S. F.; Singh, M. P.; Janso, J. E.; Clardy, J. J. Am. Chem. Soc. 2000, 122, 2116. (b) Brady, S. F.; Bondi, S. M.; Clardy, J. J. Am. Chem. Soc. 2001, 123, 9900. (c) Singh, M. P.; Janso, J. E.; Luckman, S. W.; Brady, S. F.; Clardy, J.; Greenstein, M.; Maiese, W. M. J. Antibiot. 2000, 53, 256.
16. Isolation and biological activity: (a) Brady, S. F.; Singh, M. P.; Janso, J. E.; Clardy, J. J. Am. Chem. Soc. 2000, 122, 2116. (b) Brady, S. F.; Bondi, S. M.; Clardy, J. J. Am. Chem. Soc. 2001, 123, 9900. (c) Singh, M. P.; Janso, J. E.; Luckman, S. W.; Brady, S. F.; Clardy, J.; Greenstein, M.; Maiese, W. M. J. Antibiot. 2000, 53, 256.
17. Total and formal syntheses: (a) Tan, D. S.; Dudley, G. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2185. (b) Lin, S.; Dudley, G. B.; Tan, D. S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2188. (c) Shi, B.; Hawryluk, N. A.; Snider, B. B.; J. Org. Chem. 2003, 68, 1030.
18. Total and formal syntheses: (a) Tan, D. S.; Dudley, G. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2185. (b) Lin, S.; Dudley, G. B.; Tan, D. S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2188. (c) Shi, B.; Hawryluk, N. A.; Snider, B. B.; J. Org. Chem. 2003, 68, 1030.
19. Total and formal syntheses: (a) Tan, D. S.; Dudley, G. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2185. (b) Lin, S.; Dudley, G. B.; Tan, D. S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 2188. (c) Shi, B.; Hawryluk, N. A.; Snider, B. B.; J. Org. Chem. 2003, 68, 1030.
20. For recent synthetic studies related to guanacastepene, see, inter alia: (a) Magnus, P.; Ollivier, C. Tetrahedron Lett. 2002, 43, 9605. (b) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063 (c) Nguyen, T. M.; Seifert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959. (d) Nakazaki, A.; Sharma, U.; Tius, M. A. Org. Lett. 2002, 4, 3363. (e) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2003, 44, 4233. (f) Du, X.; Chu, H. V.; Kwon, O. Org. Lett. 2003, 5, 1923. (g) Brummond K. M.; Gao, D. Org. Lett. 2003, 5, 3491. (h) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113. (i) Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 168. (j) Chiu, P.; Li, S. Org. Lett. 2004, 6, 613.
21. For recent synthetic studies related to guanacastepene, see, inter alia: (a) Magnus, P.; Ollivier, C. Tetrahedron Lett. 2002, 43, 9605. (b) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063 (c) Nguyen, T. M.; Seifert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959. (d) Nakazaki, A.; Sharma, U.; Tius, M. A. Org. Lett. 2002, 4, 3363. (e) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2003, 44, 4233. (f) Du, X.; Chu, H. V.; Kwon, O. Org. Lett. 2003, 5, 1923. (g) Brummond K. M.; Gao, D. Org. Lett. 2003, 5, 3491. (h) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113. (i) Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 168. (j) Chiu, P.; Li, S. Org. Lett. 2004, 6, 613.
22. For recent synthetic studies related to guanacastepene, see, inter alia: (a) Magnus, P.; Ollivier, C. Tetrahedron Lett. 2002, 43, 9605. (b) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063 (c) Nguyen, T. M.; Seifert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959. (d) Nakazaki, A.; Sharma, U.; Tius, M. A. Org. Lett. 2002, 4, 3363. (e) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2003, 44, 4233. (f) Du, X.; Chu, H. V.; Kwon, O. Org. Lett. 2003, 5, 1923. (g) Brummond K. M.; Gao, D. Org. Lett. 2003, 5, 3491. (h) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113. (i) Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 168. (j) Chiu, P.; Li, S. Org. Lett. 2004, 6, 613.
23. For recent synthetic studies related to guanacastepene, see, inter alia: (a) Magnus, P.; Ollivier, C. Tetrahedron Lett. 2002, 43, 9605. (b) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063 (c) Nguyen, T. M.; Seifert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959. (d) Nakazaki, A.; Sharma, U.; Tius, M. A. Org. Lett. 2002, 4, 3363. (e) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2003, 44, 4233. (f) Du, X.; Chu, H. V.; Kwon, O. Org. Lett. 2003, 5, 1923. (g) Brummond K. M.; Gao, D. Org. Lett. 2003, 5, 3491. (h) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113. (i) Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 168. (j) Chiu, P.; Li, S. Org. Lett. 2004, 6, 613.
24. For recent synthetic studies related to guanacastepene, see, inter alia: (a) Magnus, P.; Ollivier, C. Tetrahedron Lett. 2002, 43, 9605. (b) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063 (c) Nguyen, T. M.; Seifert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959. (d) Nakazaki, A.; Sharma, U.; Tius, M. A. Org. Lett. 2002, 4, 3363. (e) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2003, 44, 4233. (f) Du, X.; Chu, H. V.; Kwon, O. Org. Lett. 2003, 5, 1923. (g) Brummond K. M.; Gao, D. Org. Lett. 2003, 5, 3491. (h) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113. (i) Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 168. (j) Chiu, P.; Li, S. Org. Lett. 2004, 6, 613.
25. For recent synthetic studies related to guanacastepene, see, inter alia: (a) Magnus, P.; Ollivier, C. Tetrahedron Lett. 2002, 43, 9605. (b) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063 (c) Nguyen, T. M.; Seifert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959. (d) Nakazaki, A.; Sharma, U.; Tius, M. A. Org. Lett. 2002, 4, 3363. (e) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2003, 44, 4233. (f) Du, X.; Chu, H. V.; Kwon, O. Org. Lett. 2003, 5, 1923. (g) Brummond K. M.; Gao, D. Org. Lett. 2003, 5, 3491. (h) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113. (i) Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 168. (j) Chiu, P.; Li, S. Org. Lett. 2004, 6, 613.
26. For recent synthetic studies related to guanacastepene, see, inter alia: (a) Magnus, P.; Ollivier, C. Tetrahedron Lett. 2002, 43, 9605. (b) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063 (c) Nguyen, T. M.; Seifert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959. (d) Nakazaki, A.; Sharma, U.; Tius, M. A. Org. Lett. 2002, 4, 3363. (e) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2003, 44, 4233. (f) Du, X.; Chu, H. V.; Kwon, O. Org. Lett. 2003, 5, 1923. (g) Brummond K. M.; Gao, D. Org. Lett. 2003, 5, 3491. (h) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113. (i) Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 168. (j) Chiu, P.; Li, S. Org. Lett. 2004, 6, 613.
27. For recent synthetic studies related to guanacastepene, see, inter alia: (a) Magnus, P.; Ollivier, C. Tetrahedron Lett. 2002, 43, 9605. (b) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063 (c) Nguyen, T. M.; Seifert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959. (d) Nakazaki, A.; Sharma, U.; Tius, M. A. Org. Lett. 2002, 4, 3363. (e) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2003, 44, 4233. (f) Du, X.; Chu, H. V.; Kwon, O. Org. Lett. 2003, 5, 1923. (g) Brummond K. M.; Gao, D. Org. Lett. 2003, 5, 3491. (h) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113. (i) Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 168. (j) Chiu, P.; Li, S. Org. Lett. 2004, 6, 613.
28. For recent synthetic studies related to guanacastepene, see, inter alia: (a) Magnus, P.; Ollivier, C. Tetrahedron Lett. 2002, 43, 9605. (b) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063 (c) Nguyen, T. M.; Seifert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959. (d) Nakazaki, A.; Sharma, U.; Tius, M. A. Org. Lett. 2002, 4, 3363. (e) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2003, 44, 4233. (f) Du, X.; Chu, H. V.; Kwon, O. Org. Lett. 2003, 5, 1923. (g) Brummond K. M.; Gao, D. Org. Lett. 2003, 5, 3491. (h) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113. (i) Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 168. (j) Chiu, P.; Li, S. Org. Lett. 2004, 6, 613.
29. For recent synthetic studies related to guanacastepene, see, inter alia: (a) Magnus, P.; Ollivier, C. Tetrahedron Lett. 2002, 43, 9605. (b) Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063 (c) Nguyen, T. M.; Seifert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959. (d) Nakazaki, A.; Sharma, U.; Tius, M. A. Org. Lett. 2002, 4, 3363. (e) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2003, 44, 4233. (f) Du, X.; Chu, H. V.; Kwon, O. Org. Lett. 2003, 5, 1923. (g) Brummond K. M.; Gao, D. Org. Lett. 2003, 5, 3491. (h) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113. (i) Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 168. (j) Chiu, P.; Li, S. Org. Lett. 2004, 6, 613.
30. For palladium-catalyzed alkylation of dienyl epoxides, see: Trost, B. M.; Urch, C. J.; Hung, M.-H. Tetrahedron Lett. 1986, 27, 4949.
31. Boyer, F.-D.; Hanna, I. Tetrahedron Lett. 2002, 43, 7469.
32. 6 diastereomers 8 and 9 exhibit strike differences in their NMR spectra. In particular, while 9 showed sharp signals for all carbon atoms, many of its diastereomer were broad or hardly observed (see the Supporting Information).
33. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
34. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
35. While cleavage of the silyl ether in 10 with TBAF in THF was very easy (0°C, 30 min, quantitative yield), complete conversion of 11 to 13 necessitated longer time and higher temperature (17 h, rt).
36. The structure of 16 were deduced from its NMR spectra in comparison with those 8 and 9 (see ref 12).
37. 8c: Details concerning the preparation of bicylic dienes 27 and 30 will be reported shortly.
38. 8c
39. For 1,2-asymmetric additions of alcohols to isoprene monoepoxide, see: Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
40. NMR spectra of 31 are identical to those described in ref 4c. The regio- and stereochemistry of 33 was determined as follows: oxidation of the inseparable mixture of diastereomers afforded a single enone whose structure was deduced from spectroscopic data.