Concise synthesis of cis- and trans-theaspirones via oxonium ion-initiated pinacol ring expansion

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 1119-1121

  Paquette, Leo A ^a   Lanter, James C ^a,b   Wang, Hui Ling ^a,c  

^a OHIO STATE UNIVERSITY   (United States)

^b GANN ^*

^c NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000254625     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951890h     Document Type: Article

References (43)

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28. For preparation of the lactol, consult: (a) Arth, G. E. J. Am. Chem. Soc. 1953, 75, 2413. (b) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6335. (c) Ishii, Y.; Yoshida, T.; Yamawaki, K.; Ogawa, M. J. Org. Chem. 1988, 53, 5549. (d) Schmitt, A.; Reissig, H. U. Synlett 1990, 40. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84. (f) Masuyama, Y.; Kobayashi, Y.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1994, 1123. (g) Botteghi, C. Gazz. Chim. Ital. 1975, 105, 233. (h) Mori, K. Tetrahedron 1975, 31, 3011. (i) Schuler, H. R.; Slessor, K. N Can. J. Chem. 1977, 55, 3280. For synthesis of the dihydrofuran, see: (j) Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W., Waykole, L. Tetrahedron 1985, 41, 4873. (k) Ducoux, J. P.; Le Menez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
29. For preparation of the lactol, consult: (a) Arth, G. E. J. Am. Chem. Soc. 1953, 75, 2413. (b) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6335. (c) Ishii, Y.; Yoshida, T.; Yamawaki, K.; Ogawa, M. J. Org. Chem. 1988, 53, 5549. (d) Schmitt, A.; Reissig, H. U. Synlett 1990, 40. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84. (f) Masuyama, Y.; Kobayashi, Y.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1994, 1123. (g) Botteghi, C. Gazz. Chim. Ital. 1975, 105, 233. (h) Mori, K. Tetrahedron 1975, 31, 3011. (i) Schuler, H. R.; Slessor, K. N Can. J. Chem. 1977, 55, 3280. For synthesis of the dihydrofuran, see: (j) Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W., Waykole, L. Tetrahedron 1985, 41, 4873. (k) Ducoux, J. P.; Le Menez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
30. For preparation of the lactol, consult: (a) Arth, G. E. J. Am. Chem. Soc. 1953, 75, 2413. (b) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6335. (c) Ishii, Y.; Yoshida, T.; Yamawaki, K.; Ogawa, M. J. Org. Chem. 1988, 53, 5549. (d) Schmitt, A.; Reissig, H. U. Synlett 1990, 40. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84. (f) Masuyama, Y.; Kobayashi, Y.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1994, 1123. (g) Botteghi, C. Gazz. Chim. Ital. 1975, 105, 233. (h) Mori, K. Tetrahedron 1975, 31, 3011. (i) Schuler, H. R.; Slessor, K. N Can. J. Chem. 1977, 55, 3280. For synthesis of the dihydrofuran, see: (j) Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W., Waykole, L. Tetrahedron 1985, 41, 4873. (k) Ducoux, J. P.; Le Menez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
31. For preparation of the lactol, consult: (a) Arth, G. E. J. Am. Chem. Soc. 1953, 75, 2413. (b) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6335. (c) Ishii, Y.; Yoshida, T.; Yamawaki, K.; Ogawa, M. J. Org. Chem. 1988, 53, 5549. (d) Schmitt, A.; Reissig, H. U. Synlett 1990, 40. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84. (f) Masuyama, Y.; Kobayashi, Y.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1994, 1123. (g) Botteghi, C. Gazz. Chim. Ital. 1975, 105, 233. (h) Mori, K. Tetrahedron 1975, 31, 3011. (i) Schuler, H. R.; Slessor, K. N Can. J. Chem. 1977, 55, 3280. For synthesis of the dihydrofuran, see: (j) Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W., Waykole, L. Tetrahedron 1985, 41, 4873. (k) Ducoux, J. P.; Le Menez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
32. For preparation of the lactol, consult: (a) Arth, G. E. J. Am. Chem. Soc. 1953, 75, 2413. (b) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6335. (c) Ishii, Y.; Yoshida, T.; Yamawaki, K.; Ogawa, M. J. Org. Chem. 1988, 53, 5549. (d) Schmitt, A.; Reissig, H. U. Synlett 1990, 40. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84. (f) Masuyama, Y.; Kobayashi, Y.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1994, 1123. (g) Botteghi, C. Gazz. Chim. Ital. 1975, 105, 233. (h) Mori, K. Tetrahedron 1975, 31, 3011. (i) Schuler, H. R.; Slessor, K. N Can. J. Chem. 1977, 55, 3280. For synthesis of the dihydrofuran, see: (j) Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W., Waykole, L. Tetrahedron 1985, 41, 4873. (k) Ducoux, J. P.; Le Menez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
33. For preparation of the lactol, consult: (a) Arth, G. E. J. Am. Chem. Soc. 1953, 75, 2413. (b) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6335. (c) Ishii, Y.; Yoshida, T.; Yamawaki, K.; Ogawa, M. J. Org. Chem. 1988, 53, 5549. (d) Schmitt, A.; Reissig, H. U. Synlett 1990, 40. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84. (f) Masuyama, Y.; Kobayashi, Y.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1994, 1123. (g) Botteghi, C. Gazz. Chim. Ital. 1975, 105, 233. (h) Mori, K. Tetrahedron 1975, 31, 3011. (i) Schuler, H. R.; Slessor, K. N Can. J. Chem. 1977, 55, 3280. For synthesis of the dihydrofuran, see: (j) Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W., Waykole, L. Tetrahedron 1985, 41, 4873. (k) Ducoux, J. P.; Le Menez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
34. For preparation of the lactol, consult: (a) Arth, G. E. J. Am. Chem. Soc. 1953, 75, 2413. (b) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6335. (c) Ishii, Y.; Yoshida, T.; Yamawaki, K.; Ogawa, M. J. Org. Chem. 1988, 53, 5549. (d) Schmitt, A.; Reissig, H. U. Synlett 1990, 40. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84. (f) Masuyama, Y.; Kobayashi, Y.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1994, 1123. (g) Botteghi, C. Gazz. Chim. Ital. 1975, 105, 233. (h) Mori, K. Tetrahedron 1975, 31, 3011. (i) Schuler, H. R.; Slessor, K. N Can. J. Chem. 1977, 55, 3280. For synthesis of the dihydrofuran, see: (j) Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W., Waykole, L. Tetrahedron 1985, 41, 4873. (k) Ducoux, J. P.; Le Menez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
35. For preparation of the lactol, consult: (a) Arth, G. E. J. Am. Chem. Soc. 1953, 75, 2413. (b) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6335. (c) Ishii, Y.; Yoshida, T.; Yamawaki, K.; Ogawa, M. J. Org. Chem. 1988, 53, 5549. (d) Schmitt, A.; Reissig, H. U. Synlett 1990, 40. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84. (f) Masuyama, Y.; Kobayashi, Y.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1994, 1123. (g) Botteghi, C. Gazz. Chim. Ital. 1975, 105, 233. (h) Mori, K. Tetrahedron 1975, 31, 3011. (i) Schuler, H. R.; Slessor, K. N Can. J. Chem. 1977, 55, 3280. For synthesis of the dihydrofuran, see: (j) Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W., Waykole, L. Tetrahedron 1985, 41, 4873. (k) Ducoux, J. P.; Le Menez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
36. For preparation of the lactol, consult: (a) Arth, G. E. J. Am. Chem. Soc. 1953, 75, 2413. (b) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6335. (c) Ishii, Y.; Yoshida, T.; Yamawaki, K.; Ogawa, M. J. Org. Chem. 1988, 53, 5549. (d) Schmitt, A.; Reissig, H. U. Synlett 1990, 40. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84. (f) Masuyama, Y.; Kobayashi, Y.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1994, 1123. (g) Botteghi, C. Gazz. Chim. Ital. 1975, 105, 233. (h) Mori, K. Tetrahedron 1975, 31, 3011. (i) Schuler, H. R.; Slessor, K. N Can. J. Chem. 1977, 55, 3280. For synthesis of the dihydrofuran, see: (j) Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W., Waykole, L. Tetrahedron 1985, 41, 4873. (k) Ducoux, J. P.; Le Menez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
37. For preparation of the lactol, consult: (a) Arth, G. E. J. Am. Chem. Soc. 1953, 75, 2413. (b) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6335. (c) Ishii, Y.; Yoshida, T.; Yamawaki, K.; Ogawa, M. J. Org. Chem. 1988, 53, 5549. (d) Schmitt, A.; Reissig, H. U. Synlett 1990, 40. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84. (f) Masuyama, Y.; Kobayashi, Y.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1994, 1123. (g) Botteghi, C. Gazz. Chim. Ital. 1975, 105, 233. (h) Mori, K. Tetrahedron 1975, 31, 3011. (i) Schuler, H. R.; Slessor, K. N Can. J. Chem. 1977, 55, 3280. For synthesis of the dihydrofuran, see: (j) Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W., Waykole, L. Tetrahedron 1985, 41, 4873. (k) Ducoux, J. P.; Le Menez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
38. For preparation of the lactol, consult: (a) Arth, G. E. J. Am. Chem. Soc. 1953, 75, 2413. (b) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6335. (c) Ishii, Y.; Yoshida, T.; Yamawaki, K.; Ogawa, M. J. Org. Chem. 1988, 53, 5549. (d) Schmitt, A.; Reissig, H. U. Synlett 1990, 40. (e) Ragoussis, V.; Theodorou, V. Synthesis 1993, 84. (f) Masuyama, Y.; Kobayashi, Y.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1994, 1123. (g) Botteghi, C. Gazz. Chim. Ital. 1975, 105, 233. (h) Mori, K. Tetrahedron 1975, 31, 3011. (i) Schuler, H. R.; Slessor, K. N Can. J. Chem. 1977, 55, 3280. For synthesis of the dihydrofuran, see: (j) Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W., Waykole, L. Tetrahedron 1985, 41, 4873. (k) Ducoux, J. P.; Le Menez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
39. Purchased from the Aldrich Chemical Co.
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