Expedient synthesis of a highly substituted tropolone via a 3-oxidopyrylium [5+2] cycloaddition reaction

Tetrahedron Letters

Volumn 44, Issue 24, 2003, Pages 4543-4545

  Baldwin, Jack E ^a   Mayweg, Alexander V W ^a   Pritchard, Gareth J ^b   Adlington, Robert M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 OXIDOPYRYLIUM; ACRONITRILE; ALLYL COMPOUND; NITRILE; OXIDE; TROPOLONE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL PROCEDURES; CYCLOADDITION; GEL CHROMATOGRAPHY; INFRARED RADIATION; ISOMER; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0038742052     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00987-0     Document Type: Article

References (37)

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15. For recent work on colchicine analogues, see: (a) Lee, K.-H. Med. Res. Rev. 1999, 19, 569; For recent tropolone syntheses, see: (b) Banwell, M. G. Pure Appl. Chem. 1996, 68, 539; (c) Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 52, 4851; (d) Banwell, M. G.; Lambert, J. N.; Gravatt, G. L. J. Chem. Soc., Perkin Trans. 1 1993, 2817; (e) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675; (f) Soung, M.-G.; Matsui, M.; Kitahara, T. Tetrahedron 2000, 56, 7741; (g) Lee, J. C.; Jin, S.-J.; Cha, J. K. J. Org. Chem. 1998, 63, 2804; (h) Boger, D. L.; Ichikawa, S.; Jiang, H. J. Am. Chem. Soc. 2000, 122, 12169.
16. For recent work on colchicine analogues, see: (a) Lee, K.-H. Med. Res. Rev. 1999, 19, 569; For recent tropolone syntheses, see: (b) Banwell, M. G. Pure Appl. Chem. 1996, 68, 539; (c) Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 52, 4851; (d) Banwell, M. G.; Lambert, J. N.; Gravatt, G. L. J. Chem. Soc., Perkin Trans. 1 1993, 2817; (e) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675; (f) Soung, M.-G.; Matsui, M.; Kitahara, T. Tetrahedron 2000, 56, 7741; (g) Lee, J. C.; Jin, S.-J.; Cha, J. K. J. Org. Chem. 1998, 63, 2804; (h) Boger, D. L.; Ichikawa, S.; Jiang, H. J. Am. Chem. Soc. 2000, 122, 12169.
17. For recent work on colchicine analogues, see: (a) Lee, K.-H. Med. Res. Rev. 1999, 19, 569; For recent tropolone syntheses, see: (b) Banwell, M. G. Pure Appl. Chem. 1996, 68, 539; (c) Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 52, 4851; (d) Banwell, M. G.; Lambert, J. N.; Gravatt, G. L. J. Chem. Soc., Perkin Trans. 1 1993, 2817; (e) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675; (f) Soung, M.-G.; Matsui, M.; Kitahara, T. Tetrahedron 2000, 56, 7741; (g) Lee, J. C.; Jin, S.-J.; Cha, J. K. J. Org. Chem. 1998, 63, 2804; (h) Boger, D. L.; Ichikawa, S.; Jiang, H. J. Am. Chem. Soc. 2000, 122, 12169.
18. For recent work on colchicine analogues, see: (a) Lee, K.-H. Med. Res. Rev. 1999, 19, 569; For recent tropolone syntheses, see: (b) Banwell, M. G. Pure Appl. Chem. 1996, 68, 539; (c) Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 52, 4851; (d) Banwell, M. G.; Lambert, J. N.; Gravatt, G. L. J. Chem. Soc., Perkin Trans. 1 1993, 2817; (e) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675; (f) Soung, M.-G.; Matsui, M.; Kitahara, T. Tetrahedron 2000, 56, 7741; (g) Lee, J. C.; Jin, S.-J.; Cha, J. K. J. Org. Chem. 1998, 63, 2804; (h) Boger, D. L.; Ichikawa, S.; Jiang, H. J. Am. Chem. Soc. 2000, 122, 12169.
19. For recent work on colchicine analogues, see: (a) Lee, K.-H. Med. Res. Rev. 1999, 19, 569; For recent tropolone syntheses, see: (b) Banwell, M. G. Pure Appl. Chem. 1996, 68, 539; (c) Banwell, M. G.; Onrust, R. Tetrahedron Lett. 1985, 52, 4851; (d) Banwell, M. G.; Lambert, J. N.; Gravatt, G. L. J. Chem. Soc., Perkin Trans. 1 1993, 2817; (e) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675; (f) Soung, M.-G.; Matsui, M.; Kitahara, T. Tetrahedron 2000, 56, 7741; (g) Lee, J. C.; Jin, S.-J.; Cha, J. K. J. Org. Chem. 1998, 63, 2804; (h) Boger, D. L.; Ichikawa, S.; Jiang, H. J. Am. Chem. Soc. 2000, 122, 12169.
20. Baldwin J.E., Mayweg A.V.W., Neumann K., Pritchard G.J. Org. Lett. 1:1999;1933.
21. Adlington R.M., Baldwin J.E., Mayweg A.V.W., Pritchard G.J. Org. Lett. 4:2002;3009.
22. For further examples of 1,3-dipolar cycloadditions with 3-oxidopyrylium species, see: (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359; (b) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361; (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261; (d) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1983, 666; (e) Sammes, P. G.; Street, L. J. J. Chem. Res. 1984, 196; (f) Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725; (g) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1986, 281; (h) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353; (i) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135; (j) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954; (k) Magnus, P.; Diorazio, L.; Donohoe, T. J.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. Tetrahedron 1996, 52, 14147.
23. For further examples of 1,3-dipolar cycloadditions with 3-oxidopyrylium species, see: (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359; (b) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361; (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261; (d) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1983, 666; (e) Sammes, P. G.; Street, L. J. J. Chem. Res. 1984, 196; (f) Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725; (g) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1986, 281; (h) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353; (i) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135; (j) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954; (k) Magnus, P.; Diorazio, L.; Donohoe, T. J.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. Tetrahedron 1996, 52, 14147.
24. For further examples of 1,3-dipolar cycloadditions with 3-oxidopyrylium species, see: (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359; (b) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361; (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261; (d) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1983, 666; (e) Sammes, P. G.; Street, L. J. J. Chem. Res. 1984, 196; (f) Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725; (g) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1986, 281; (h) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353; (i) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135; (j) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954; (k) Magnus, P.; Diorazio, L.; Donohoe, T. J.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. Tetrahedron 1996, 52, 14147.
25. For further examples of 1,3-dipolar cycloadditions with 3-oxidopyrylium species, see: (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359; (b) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361; (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261; (d) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1983, 666; (e) Sammes, P. G.; Street, L. J. J. Chem. Res. 1984, 196; (f) Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725; (g) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1986, 281; (h) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353; (i) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135; (j) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954; (k) Magnus, P.; Diorazio, L.; Donohoe, T. J.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. Tetrahedron 1996, 52, 14147.
26. For further examples of 1,3-dipolar cycloadditions with 3-oxidopyrylium species, see: (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359; (b) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361; (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261; (d) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1983, 666; (e) Sammes, P. G.; Street, L. J. J. Chem. Res. 1984, 196; (f) Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725; (g) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1986, 281; (h) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353; (i) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135; (j) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954; (k) Magnus, P.; Diorazio, L.; Donohoe, T. J.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. Tetrahedron 1996, 52, 14147.
27. For further examples of 1,3-dipolar cycloadditions with 3-oxidopyrylium species, see: (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359; (b) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361; (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261; (d) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1983, 666; (e) Sammes, P. G.; Street, L. J. J. Chem. Res. 1984, 196; (f) Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725; (g) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1986, 281; (h) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353; (i) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135; (j) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954; (k) Magnus, P.; Diorazio, L.; Donohoe, T. J.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. Tetrahedron 1996, 52, 14147.
28. For further examples of 1,3-dipolar cycloadditions with 3-oxidopyrylium species, see: (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359; (b) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361; (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261; (d) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1983, 666; (e) Sammes, P. G.; Street, L. J. J. Chem. Res. 1984, 196; (f) Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725; (g) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1986, 281; (h) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353; (i) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135; (j) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954; (k) Magnus, P.; Diorazio, L.; Donohoe, T. J.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. Tetrahedron 1996, 52, 14147.
29. For further examples of 1,3-dipolar cycloadditions with 3-oxidopyrylium species, see: (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359; (b) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361; (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261; (d) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1983, 666; (e) Sammes, P. G.; Street, L. J. J. Chem. Res. 1984, 196; (f) Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725; (g) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1986, 281; (h) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353; (i) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135; (j) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954; (k) Magnus, P.; Diorazio, L.; Donohoe, T. J.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. Tetrahedron 1996, 52, 14147.
30. For further examples of 1,3-dipolar cycloadditions with 3-oxidopyrylium species, see: (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359; (b) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361; (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261; (d) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1983, 666; (e) Sammes, P. G.; Street, L. J. J. Chem. Res. 1984, 196; (f) Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725; (g) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1986, 281; (h) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353; (i) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135; (j) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954; (k) Magnus, P.; Diorazio, L.; Donohoe, T. J.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. Tetrahedron 1996, 52, 14147.
31. For further examples of 1,3-dipolar cycloadditions with 3-oxidopyrylium species, see: (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359; (b) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361; (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261; (d) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1983, 666; (e) Sammes, P. G.; Street, L. J. J. Chem. Res. 1984, 196; (f) Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725; (g) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1986, 281; (h) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353; (i) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135; (j) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954; (k) Magnus, P.; Diorazio, L.; Donohoe, T. J.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. Tetrahedron 1996, 52, 14147.
32. For further examples of 1,3-dipolar cycloadditions with 3-oxidopyrylium species, see: (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359; (b) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361; (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261; (d) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1983, 666; (e) Sammes, P. G.; Street, L. J. J. Chem. Res. 1984, 196; (f) Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725; (g) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1986, 281; (h) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353; (i) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135; (j) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954; (k) Magnus, P.; Diorazio, L.; Donohoe, T. J.; Giles, M.; Pye, P.; Tarrant, J.; Thom, S. Tetrahedron 1996, 52, 14147.
33. 3Si requires 308.1681.
34. A closely related cleavage of an oxy-bridge beta to a nitrile function in a [3.2.1] bicycle was previously reported. See: Marshall K.A., Mapp A.K., Heathcock C.H. J. Org. Chem. 61:1996;9135.
35. The stereochemistry of 12 was assigned using NOE NMR spectroscopy.
36. 2, IBX, PDC, PCC.
37. 3Si requires 320.1682.