Oxetane formation by 1,3-migration of benzyloxy group in 7- oxabicyclo[2.2.1]hept-2-yl cations: Synthesis of 4,7- dioxatricyclo[3.2.1.O3,6]octane and 2-oxabicyclo[2.2.2]octane encrusted in the 1,4:5,8-diepoxy-perhydrophenanthrene ring system

Heterocycles

Volumn 52, Issue 1, 2000, Pages 171-183

  Mosimann, Hervé ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; OCTANE; OXETANE DERIVATIVE; PHENANTHRENE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; EPOXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033984105     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-s4     Document Type: Article

References (56)

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10. B. Kühne, H.-P. Hanssen, W.-R. Abraham, and V. Wray, Phytochemistry, 1991, 30, 1463.
11. H. Ginda, T. Kusumi, M. O. Ishitsuka, H. Kakisawa, Z. Weijie, C. Jun, and G. Y. Tian, Tetrahedron Lett., 1988, 29, 4603; B. Li, F-D. Niu, Z-W. Lin, H-J. Zhang, D-Z. Wang, and H-D. Sun, Phytochemistry, 1991, 30, 3815.
12. H. Ginda, T. Kusumi, M. O. Ishitsuka, H. Kakisawa, Z. Weijie, C. Jun, and G. Y. Tian, Tetrahedron Lett., 1988, 29, 4603; B. Li, F-D. Niu, Z-W. Lin, H-J. Zhang, D-Z. Wang, and H-D. Sun, Phytochemistry, 1991, 30, 3815.
13. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
14. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
15. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
16. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
17. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
18. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
19. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
20. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
21. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
22. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
23. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
24. For other examples of natural products containing 2-oxabicyclo[2.2.2]octane moieties, see e.g.: G. Cuevas, O. Collera, F. García, J. Cárdenas, E. Maldonado, and A. Ortega, Phytochernistry, 1987, 26, 2019; the granaticins: W. Keller-Schierlein, M. Brufani, and S. Barcza, Helv. Chim. Acta, 1968, 51, 1257; M. Brufani and M. Dobler, Helv. Chim. Acta 1968, 51, 1269; M. L. Gilpin, S. J. Box, and A. L. Elson, J. Antibiot., 1988, 41, 512; heterocurvistone, constituent of Heterotropa curvistigma: M. Niwa, Y. Sugie, and S. Yamamura, Phytochemistry, 1981, 20, 1137; spironippol a constituent of the red alga Laurencia nipponica Yamada: A. Fukuzawa, C. M. Shea, T. Masamune, A. Furusaki, C. Katayama, and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4087; sesquicineol, a bisabolene oxide found in plants with antiinflamatory activity: F. Bohlmann and C. Zdero, Phytochemistry, 1982, 21, 1697; J. de Pascual-T., M. L. Hernández, J. R. Moran, C. Caballero, J. Anaya, and V. Alcazar, Tetrahedron, 1988, 44, 5109; miltipolone, a constituent of Salvia miltiorrhiza Bunge ("Tanjin" folk medicine): G. Haro, M. Mori, M. O. Ishitsuka, T. Kusumi, Y. Inouye, and H. Kakisawa, Bull. Chem. Soc. Jpn., 1991, 64, 3422; abietane diterpene derivatives from Salvia mellifera: J. C. Lius, L. San Andés, Phytochemistry, 1993, 33, 635; pauciflorol acetate isolated from Sericostoma pauciflorum: S. A. M. Ayatollahi, Z. Ahmed, N. Afza, and A. Malik, Phytochemistry, 1992, 31, 2899; (-)-dehydro-1,8-sesquicineole and derivatives, constituent of the essential oil of Artemisia sieberi: P. Weyerstahl, S. Schneider, H. Marschall, and A. Rustaiyan, Liebigs Ann. Chem., 1993, 111.
25. A. G. González, J. D. Martín, B. González, J. L. Ravelo, C. Pérez, S. Rafii, and J. Clardy, J. Chem. Soc., Chem. Commun., 1984, 669; J. Clardy, G. Van Duyne, A. Galardo, E. Manta, J. D. Martín, C. Pérez, R. Pérez, J. L. Ravelo, M. L. Rodríguez, and G. K. Schulte, Tetrahedron Lett., 1987, 28, 6699.
26. A. G. González, J. D. Martín, B. González, J. L. Ravelo, C. Pérez, S. Rafii, and J. Clardy, J. Chem. Soc., Chem. Commun., 1984, 669; J. Clardy, G. Van Duyne, A. Galardo, E. Manta, J. D. Martín, C. Pérez, R. Pérez, J. L. Ravelo, M. L. Rodríguez, and G. K. Schulte, Tetrahedron Lett., 1987, 28, 6699.
27. H. Mosimann, P. Vogel, A. A. Pinkerton, and K. Kirschbaum, J. Org. Chem., 1997, 62, 3002.
28. L. Meerpoel, M.-M. Vrahami, J. Ancerewicz, and P. Vogel, Tetrahedron Lett., 1994, 35, 111.
29. E. Vieira and P. Vogel, Helv. Chim. Acta, 1983, 66, 1865; J.-L. Reymond and P. Vogel, Tetrahedron: Asymmetry, 1990, 1, 729; P. Vogel, D. Fattori, F. Gasparini, and C. Le Drian, Synlett, 1990, 173; see also: R. Saf, K. Faber, G. Penn, and H. Griengl, Tetrahedron, 1988, 44, 389; B. Ronan and H. B. Kagan, Tetrahedron: Asymmetry, 1991, 2, 75; E. J. Corey and T.-P. Loh, Tetrahedron Lett., 1993, 34, 3979.
30. E. Vieira and P. Vogel, Helv. Chim. Acta, 1983, 66, 1865; J.-L. Reymond and P. Vogel, Tetrahedron: Asymmetry, 1990, 1, 729; P. Vogel, D. Fattori, F. Gasparini, and C. Le Drian, Synlett, 1990, 173; see also: R. Saf, K. Faber, G. Penn, and H. Griengl, Tetrahedron, 1988, 44, 389; B. Ronan and H. B. Kagan, Tetrahedron: Asymmetry, 1991, 2, 75; E. J. Corey and T.-P. Loh, Tetrahedron Lett., 1993, 34, 3979.
31. E. Vieira and P. Vogel, Helv. Chim. Acta, 1983, 66, 1865; J.-L. Reymond and P. Vogel, Tetrahedron: Asymmetry, 1990, 1, 729; P. Vogel, D. Fattori, F. Gasparini, and C. Le Drian, Synlett, 1990, 173; see also: R. Saf, K. Faber, G. Penn, and H. Griengl, Tetrahedron, 1988, 44, 389; B. Ronan and H. B. Kagan, Tetrahedron: Asymmetry, 1991, 2, 75; E. J. Corey and T.-P. Loh, Tetrahedron Lett., 1993, 34, 3979.
32. E. Vieira and P. Vogel, Helv. Chim. Acta, 1983, 66, 1865; J.-L. Reymond and P. Vogel, Tetrahedron: Asymmetry, 1990, 1, 729; P. Vogel, D. Fattori, F. Gasparini, and C. Le Drian, Synlett, 1990, 173; see also: R. Saf, K. Faber, G. Penn, and H. Griengl, Tetrahedron, 1988, 44, 389; B. Ronan and H. B. Kagan, Tetrahedron: Asymmetry, 1991, 2, 75; E. J. Corey and T.-P. Loh, Tetrahedron Lett., 1993, 34, 3979.
33. E. Vieira and P. Vogel, Helv. Chim. Acta, 1983, 66, 1865; J.-L. Reymond and P. Vogel, Tetrahedron: Asymmetry, 1990, 1, 729; P. Vogel, D. Fattori, F. Gasparini, and C. Le Drian, Synlett, 1990, 173; see also: R. Saf, K. Faber, G. Penn, and H. Griengl, Tetrahedron, 1988, 44, 389; B. Ronan and H. B. Kagan, Tetrahedron: Asymmetry, 1991, 2, 75; E. J. Corey and T.-P. Loh, Tetrahedron Lett., 1993, 34, 3979.
34. E. Vieira and P. Vogel, Helv. Chim. Acta, 1983, 66, 1865; J.-L. Reymond and P. Vogel, Tetrahedron: Asymmetry, 1990, 1, 729; P. Vogel, D. Fattori, F. Gasparini, and C. Le Drian, Synlett, 1990, 173; see also: R. Saf, K. Faber, G. Penn, and H. Griengl, Tetrahedron, 1988, 44, 389; B. Ronan and H. B. Kagan, Tetrahedron: Asymmetry, 1991, 2, 75; E. J. Corey and T.-P. Loh, Tetrahedron Lett., 1993, 34, 3979.
35. S. Czernecki, C. Georgoulis, and C. Provelenghiou, Tetrahedron Lett., 1976, 3535,
36. 3,6]octane, see: C. Le Drian and P. Vogel, J. Org. Chemn., 1993, 58, 2328; A. A. Pinkerton, C. Le Drian, and P. Vogel, Acta Cryst., 1996, C52, 2927.
37. 3,6]octane, see: C. Le Drian and P. Vogel, J. Org. Chemn., 1993, 58, 2328; A. A. Pinkerton, C. Le Drian, and P. Vogel, Acta Cryst., 1996, C52, 2927.
38. H. Perst, in "Carbonium Ions", ed. by G. A. Olah, P. von R. Schleyer, Wiley-Interscience, 1976, Vol. V, Chapter 34, p. 1961.
39. For rearrangement in which 1,3-migration of alkoxy groups have been reported, see e.g.: C. Le Drian and P. Vogel, Helv. Chim. Acta, 1987, 70, 1703; P. G. Gassman and J. L. Marshall, Tetrahedron Lett., 1968, 2429; C. Nativi, J.-L. Reymond, and P. Vogel, Helv. Chim. Acta, 1989, 72, 882; E. Reynard, J.-L. Raymond, and P. Vogel, Synlett, 1991, 469; J.-L. Raymond, A. A. Pinkerton, and P. Vogel, J. Org. Chem., 1991, 56, 2128.
40. For rearrangement in which 1,3-migration of alkoxy groups have been reported, see e.g.: C. Le Drian and P. Vogel, Helv. Chim. Acta, 1987, 70, 1703; P. G. Gassman and J. L. Marshall, Tetrahedron Lett., 1968, 2429; C. Nativi, J.-L. Reymond, and P. Vogel, Helv. Chim. Acta, 1989, 72, 882; E. Reynard, J.-L. Raymond, and P. Vogel, Synlett, 1991, 469; J.-L. Raymond, A. A. Pinkerton, and P. Vogel, J. Org. Chem., 1991, 56, 2128.
41. For rearrangement in which 1,3-migration of alkoxy groups have been reported, see e.g.: C. Le Drian and P. Vogel, Helv. Chim. Acta, 1987, 70, 1703; P. G. Gassman and J. L. Marshall, Tetrahedron Lett., 1968, 2429; C. Nativi, J.-L. Reymond, and P. Vogel, Helv. Chim. Acta, 1989, 72, 882; E. Reynard, J.-L. Raymond, and P. Vogel, Synlett, 1991, 469; J.-L. Raymond, A. A. Pinkerton, and P. Vogel, J. Org. Chem., 1991, 56, 2128.
42. For rearrangement in which 1,3-migration of alkoxy groups have been reported, see e.g.: C. Le Drian and P. Vogel, Helv. Chim. Acta, 1987, 70, 1703; P. G. Gassman and J. L. Marshall, Tetrahedron Lett., 1968, 2429; C. Nativi, J.-L. Reymond, and P. Vogel, Helv. Chim. Acta, 1989, 72, 882; E. Reynard, J.-L. Raymond, and P. Vogel, Synlett, 1991, 469; J.-L. Raymond, A. A. Pinkerton, and P. Vogel, J. Org. Chem., 1991, 56, 2128.
43. For rearrangement in which 1,3-migration of alkoxy groups have been reported, see e.g.: C. Le Drian and P. Vogel, Helv. Chim. Acta, 1987, 70, 1703; P. G. Gassman and J. L. Marshall, Tetrahedron Lett., 1968, 2429; C. Nativi, J.-L. Reymond, and P. Vogel, Helv. Chim. Acta, 1989, 72, 882; E. Reynard, J.-L. Raymond, and P. Vogel, Synlett, 1991, 469; J.-L. Raymond, A. A. Pinkerton, and P. Vogel, J. Org. Chem., 1991, 56, 2128.
44. 2O also generates the corresponding oxetane.
45. J. C. Martin and P. D. Bartlett, J. Am. Chem. Soc., 1957, 79, 2533; Yu, K. Yur'ev and N. S. Zefirov, Zh. Obschch. Khim., 1962, 32, 773; N. S. Zefirov, R. A. Ivanova, K. M. Kecher, and Yu, K. Yur'ev, Ibid., 1965, 35, 61; H. W. Gschwend, M. J. Hillman, and B. Kisis, J. Org. Chem., 1976, 41, 104; P.-A. Carrupt and P. Vogel, J. Phys. Org. Chem., 1988, 1, 287; G. P. Moss, O. C. Keat, and G. V. Bondar, Tetrahedron Lett., 1996, 37, 2877; G. P. Moss and C. K. Ooi, J. Chem. Soc., Chem. Commun., 1992, 342; L.G. French, E. E. Fenion, and T. P. Charlton, Tetrahedron Lett., 1991, 32, 851; L. G. French and T. P. Charlton, Heterocycles, 1993, 35, 305; J. L. Reymond and P. Vogel, Chimia, 1990, 44, 342; J. B. Lambert, E. G. Larson, and K. P. Steele, J. Am. Chem. Soc., 1985, 107, 704.
46. J. C. Martin and P. D. Bartlett, J. Am. Chem. Soc., 1957, 79, 2533; Yu, K. Yur'ev and N. S. Zefirov, Zh. Obschch. Khim., 1962, 32, 773; N. S. Zefirov, R. A. Ivanova, K. M. Kecher, and Yu, K. Yur'ev, Ibid., 1965, 35, 61; H. W. Gschwend, M. J. Hillman, and B. Kisis, J. Org. Chem., 1976, 41, 104; P.-A. Carrupt and P. Vogel, J. Phys. Org. Chem., 1988, 1, 287; G. P. Moss, O. C. Keat, and G. V. Bondar, Tetrahedron Lett., 1996, 37, 2877; G. P. Moss and C. K. Ooi, J. Chem. Soc., Chem. Commun., 1992, 342; L.G. French, E. E. Fenion, and T. P. Charlton, Tetrahedron Lett., 1991, 32, 851; L. G. French and T. P. Charlton, Heterocycles, 1993, 35, 305; J. L. Reymond and P. Vogel, Chimia, 1990, 44, 342; J. B. Lambert, E. G. Larson, and K. P. Steele, J. Am. Chem. Soc., 1985, 107, 704.
47. J. C. Martin and P. D. Bartlett, J. Am. Chem. Soc., 1957, 79, 2533; Yu, K. Yur'ev and N. S. Zefirov, Zh. Obschch. Khim., 1962, 32, 773; N. S. Zefirov, R. A. Ivanova, K. M. Kecher, and Yu, K. Yur'ev, Ibid., 1965, 35, 61; H. W. Gschwend, M. J. Hillman, and B. Kisis, J. Org. Chem., 1976, 41, 104; P.-A. Carrupt and P. Vogel, J. Phys. Org. Chem., 1988, 1, 287; G. P. Moss, O. C. Keat, and G. V. Bondar, Tetrahedron Lett., 1996, 37, 2877; G. P. Moss and C. K. Ooi, J. Chem. Soc., Chem. Commun., 1992, 342; L.G. French, E. E. Fenion, and T. P. Charlton, Tetrahedron Lett., 1991, 32, 851; L. G. French and T. P. Charlton, Heterocycles, 1993, 35, 305; J. L. Reymond and P. Vogel, Chimia, 1990, 44, 342; J. B. Lambert, E. G. Larson, and K. P. Steele, J. Am. Chem. Soc., 1985, 107, 704.
48. J. C. Martin and P. D. Bartlett, J. Am. Chem. Soc., 1957, 79, 2533; Yu, K. Yur'ev and N. S. Zefirov, Zh. Obschch. Khim., 1962, 32, 773; N. S. Zefirov, R. A. Ivanova, K. M. Kecher, and Yu, K. Yur'ev, Ibid., 1965, 35, 61; H. W. Gschwend, M. J. Hillman, and B. Kisis, J. Org. Chem., 1976, 41, 104; P.-A. Carrupt and P. Vogel, J. Phys. Org. Chem., 1988, 1, 287; G. P. Moss, O. C. Keat, and G. V. Bondar, Tetrahedron Lett., 1996, 37, 2877; G. P. Moss and C. K. Ooi, J. Chem. Soc., Chem. Commun., 1992, 342; L.G. French, E. E. Fenion, and T. P. Charlton, Tetrahedron Lett., 1991, 32, 851; L. G. French and T. P. Charlton, Heterocycles, 1993, 35, 305; J. L. Reymond and P. Vogel, Chimia, 1990, 44, 342; J. B. Lambert, E. G. Larson, and K. P. Steele, J. Am. Chem. Soc., 1985, 107, 704.
49. J. C. Martin and P. D. Bartlett, J. Am. Chem. Soc., 1957, 79, 2533; Yu, K. Yur'ev and N. S. Zefirov, Zh. Obschch. Khim., 1962, 32, 773; N. S. Zefirov, R. A. Ivanova, K. M. Kecher, and Yu, K. Yur'ev, Ibid., 1965, 35, 61; H. W. Gschwend, M. J. Hillman, and B. Kisis, J. Org. Chem., 1976, 41, 104; P.-A. Carrupt and P. Vogel, J. Phys. Org. Chem., 1988, 1, 287; G. P. Moss, O. C. Keat, and G. V. Bondar, Tetrahedron Lett., 1996, 37, 2877; G. P. Moss and C. K. Ooi, J. Chem. Soc., Chem. Commun., 1992, 342; L.G. French, E. E. Fenion, and T. P. Charlton, Tetrahedron Lett., 1991, 32, 851; L. G. French and T. P. Charlton, Heterocycles, 1993, 35, 305; J. L. Reymond and P. Vogel, Chimia, 1990, 44, 342; J. B. Lambert, E. G. Larson, and K. P. Steele, J. Am. Chem. Soc., 1985, 107, 704.
50. J. C. Martin and P. D. Bartlett, J. Am. Chem. Soc., 1957, 79, 2533; Yu, K. Yur'ev and N. S. Zefirov, Zh. Obschch. Khim., 1962, 32, 773; N. S. Zefirov, R. A. Ivanova, K. M. Kecher, and Yu, K. Yur'ev, Ibid., 1965, 35, 61; H. W. Gschwend, M. J. Hillman, and B. Kisis, J. Org. Chem., 1976, 41, 104; P.-A. Carrupt and P. Vogel, J. Phys. Org. Chem., 1988, 1, 287; G. P. Moss, O. C. Keat, and G. V. Bondar, Tetrahedron Lett., 1996, 37, 2877; G. P. Moss and C. K. Ooi, J. Chem. Soc., Chem. Commun., 1992, 342; L.G. French, E. E. Fenion, and T. P. Charlton, Tetrahedron Lett., 1991, 32, 851; L. G. French and T. P. Charlton, Heterocycles, 1993, 35, 305; J. L. Reymond and P. Vogel, Chimia, 1990, 44, 342; J. B. Lambert, E. G. Larson, and K. P. Steele, J. Am. Chem. Soc., 1985, 107, 704.
51. J. C. Martin and P. D. Bartlett, J. Am. Chem. Soc., 1957, 79, 2533; Yu, K. Yur'ev and N. S. Zefirov, Zh. Obschch. Khim., 1962, 32, 773; N. S. Zefirov, R. A. Ivanova, K. M. Kecher, and Yu, K. Yur'ev, Ibid., 1965, 35, 61; H. W. Gschwend, M. J. Hillman, and B. Kisis, J. Org. Chem., 1976, 41, 104; P.-A. Carrupt and P. Vogel, J. Phys. Org. Chem., 1988, 1, 287; G. P. Moss, O. C. Keat, and G. V. Bondar, Tetrahedron Lett., 1996, 37, 2877; G. P. Moss and C. K. Ooi, J. Chem. Soc., Chem. Commun., 1992, 342; L.G. French, E. E. Fenion, and T. P. Charlton, Tetrahedron Lett., 1991, 32, 851; L. G. French and T. P. Charlton, Heterocycles, 1993, 35, 305; J. L. Reymond and P. Vogel, Chimia, 1990, 44, 342; J. B. Lambert, E. G. Larson, and K. P. Steele, J. Am. Chem. Soc., 1985, 107, 704.
52. J. C. Martin and P. D. Bartlett, J. Am. Chem. Soc., 1957, 79, 2533; Yu, K. Yur'ev and N. S. Zefirov, Zh. Obschch. Khim., 1962, 32, 773; N. S. Zefirov, R. A. Ivanova, K. M. Kecher, and Yu, K. Yur'ev, Ibid., 1965, 35, 61; H. W. Gschwend, M. J. Hillman, and B. Kisis, J. Org. Chem., 1976, 41, 104; P.-A. Carrupt and P. Vogel, J. Phys. Org. Chem., 1988, 1, 287; G. P. Moss, O. C. Keat, and G. V. Bondar, Tetrahedron Lett., 1996, 37, 2877; G. P. Moss and C. K. Ooi, J. Chem. Soc., Chem. Commun., 1992, 342; L.G. French, E. E. Fenion, and T. P. Charlton, Tetrahedron Lett., 1991, 32, 851; L. G. French and T. P. Charlton, Heterocycles, 1993, 35, 305; J. L. Reymond and P. Vogel, Chimia, 1990, 44, 342; J. B. Lambert, E. G. Larson, and K. P. Steele, J. Am. Chem. Soc., 1985, 107, 704.
53. J. C. Martin and P. D. Bartlett, J. Am. Chem. Soc., 1957, 79, 2533; Yu, K. Yur'ev and N. S. Zefirov, Zh. Obschch. Khim., 1962, 32, 773; N. S. Zefirov, R. A. Ivanova, K. M. Kecher, and Yu, K. Yur'ev, Ibid., 1965, 35, 61; H. W. Gschwend, M. J. Hillman, and B. Kisis, J. Org. Chem., 1976, 41, 104; P.-A. Carrupt and P. Vogel, J. Phys. Org. Chem., 1988, 1, 287; G. P. Moss, O. C. Keat, and G. V. Bondar, Tetrahedron Lett., 1996, 37, 2877; G. P. Moss and C. K. Ooi, J. Chem. Soc., Chem. Commun., 1992, 342; L.G. French, E. E. Fenion, and T. P. Charlton, Tetrahedron Lett., 1991, 32, 851; L. G. French and T. P. Charlton, Heterocycles, 1993, 35, 305; J. L. Reymond and P. Vogel, Chimia, 1990, 44, 342; J. B. Lambert, E. G. Larson, and K. P. Steele, J. Am. Chem. Soc., 1985, 107, 704.
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