3-Hydroxy-4-pyrones as precursors of 4-methoxy-3-oxidopyridinium ylides. An expeditious entry to highly substituted 8-azabicyclo[3.2.1]octanes

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6114-6120

  Rumbo, Antonio ^a   Mouriño, Antonio ^a   Castedo, Luis ^a   Mascareñas, José L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 4 PYRONE DERIVATIVE; 8 AZABICYCLO[3.2.1]OCTANE DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029815587     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960854v     Document Type: Article

References (51)

1. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
2. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
3. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
4. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
5. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
6. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
7. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
8. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
9. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
10. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
11. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
12. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
13. For [4C + 3C] cycloadditions, see: (a) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. In Natural Product Synthesis through Pericyclic Reactions; Marjorie, C. C., Ed.; ACS Monograph; American Chemical Society: Washington, DC, 1983; pp 255-265. (b) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 5.1. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI: Greenwich, 1995; Vol 4. (e) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830. For [5C + 2C] annulations, see: (f) Sammes, P. G. Gazz. Chim. Ital. 1986, 119, 109. (g) Thomas, E. J.; Mortlock, S. V.; Seckington, J. K. J. Chem. Soc., Perkin Trans. 1 1988, 2305. (h) Padwa, A.; Fryxell, G. E.; Zhi, H. J. Am. Chem. Soc. 1990, 112, 3100. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956. (j) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267. (k) Wender, P. A.; Mascareñas, J. L. Tetrahedron Lett. 1992, 33, 2115. (l) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567. (m) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588.
14. Rumbo, A.; Castedo, L.; Mouriño, A.; Mascareñas, J. L. J. Org. Chem. 1993, 58, 5585.
15. These cycloadducts can be transformed into sesquiterpene precursors or stereochemically rich 2,3,5-trisubstituted tetrahydrofurans: Rumbo, A.; Castedo, L.; Mourino, A.; Mascarenas, J. L. Unpublished results.
16. Several recent articles concerning the preparation of biologically relevant chelators describe the transformation of 3-hydroxy-4-pyrones into 3-hydroxy-4-pyridones: (a) Nelson, W. O.; Karpishing, T. B.; Rettig, S. J.; Orvig, C. Can. J. Chem. 1988, 66, 123. (b) Dobbin, P. S.; Hider, R. C.; Hall, A. D.; Taylor, P. D.; Sarpong, P.; Porter, J. B.; Xiao, G.; Van der Helm, D. J. Med. Chem. 1993, 36, 2448. (c) Kontoghiorghes, G. J.; Sheppard, L. Inorg. Chim. Acta 1987, 136, L11-L12. (d) Molenda, J. J.; Jones, M. M.; Johnston, D. S.; Walker, E. M.; Cannon, D. J. J. Med. Chem. 1994, 37, 4363.
17. Several recent articles concerning the preparation of biologically relevant chelators describe the transformation of 3-hydroxy-4-pyrones into 3-hydroxy-4-pyridones: (a) Nelson, W. O.; Karpishing, T. B.; Rettig, S. J.; Orvig, C. Can. J. Chem. 1988, 66, 123. (b) Dobbin, P. S.; Hider, R. C.; Hall, A. D.; Taylor, P. D.; Sarpong, P.; Porter, J. B.; Xiao, G.; Van der Helm, D. J. Med. Chem. 1993, 36, 2448. (c) Kontoghiorghes, G. J.; Sheppard, L. Inorg. Chim. Acta 1987, 136, L11-L12. (d) Molenda, J. J.; Jones, M. M.; Johnston, D. S.; Walker, E. M.; Cannon, D. J. J. Med. Chem. 1994, 37, 4363.
18. Several recent articles concerning the preparation of biologically relevant chelators describe the transformation of 3-hydroxy-4-pyrones into 3-hydroxy-4-pyridones: (a) Nelson, W. O.; Karpishing, T. B.; Rettig, S. J.; Orvig, C. Can. J. Chem. 1988, 66, 123. (b) Dobbin, P. S.; Hider, R. C.; Hall, A. D.; Taylor, P. D.; Sarpong, P.; Porter, J. B.; Xiao, G.; Van der Helm, D. J. Med. Chem. 1993, 36, 2448. (c) Kontoghiorghes, G. J.; Sheppard, L. Inorg. Chim. Acta 1987, 136, L11-L12. (d) Molenda, J. J.; Jones, M. M.; Johnston, D. S.; Walker, E. M.; Cannon, D. J. J. Med. Chem. 1994, 37, 4363.
19. Several recent articles concerning the preparation of biologically relevant chelators describe the transformation of 3-hydroxy-4-pyrones into 3-hydroxy-4-pyridones: (a) Nelson, W. O.; Karpishing, T. B.; Rettig, S. J.; Orvig, C. Can. J. Chem. 1988, 66, 123. (b) Dobbin, P. S.; Hider, R. C.; Hall, A. D.; Taylor, P. D.; Sarpong, P.; Porter, J. B.; Xiao, G.; Van der Helm, D. J. Med. Chem. 1993, 36, 2448. (c) Kontoghiorghes, G. J.; Sheppard, L. Inorg. Chim. Acta 1987, 136, L11-L12. (d) Molenda, J. J.; Jones, M. M.; Johnston, D. S.; Walker, E. M.; Cannon, D. J. J. Med. Chem. 1994, 37, 4363.
20. For leading references to tropane alkaloids, see: (a) Fodor, G.; Dharanipragada, R. Nat. Prod. Rep. 1994, 11, 443. (b) Lounasma, M. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 33, pp 1-81. (c) Lounasma, M.; Tamminen, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 44, p 1. (d) Stoelwinder, J.; Roberti, M.; Kozikowski, A. P.; Johnson, K. M.; Bergmann, J. S. Bioorg. Med. Chem. Lett. 1994, 4, 303.
21. For leading references to tropane alkaloids, see: (a) Fodor, G.; Dharanipragada, R. Nat. Prod. Rep. 1994, 11, 443. (b) Lounasma, M. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 33, pp 1-81. (c) Lounasma, M.; Tamminen, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 44, p 1. (d) Stoelwinder, J.; Roberti, M.; Kozikowski, A. P.; Johnson, K. M.; Bergmann, J. S. Bioorg. Med. Chem. Lett. 1994, 4, 303.
22. For leading references to tropane alkaloids, see: (a) Fodor, G.; Dharanipragada, R. Nat. Prod. Rep. 1994, 11, 443. (b) Lounasma, M. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 33, pp 1-81. (c) Lounasma, M.; Tamminen, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 44, p 1. (d) Stoelwinder, J.; Roberti, M.; Kozikowski, A. P.; Johnson, K. M.; Bergmann, J. S. Bioorg. Med. Chem. Lett. 1994, 4, 303.
23. For leading references to tropane alkaloids, see: (a) Fodor, G.; Dharanipragada, R. Nat. Prod. Rep. 1994, 11, 443. (b) Lounasma, M. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 33, pp 1-81. (c) Lounasma, M.; Tamminen, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 44, p 1. (d) Stoelwinder, J.; Roberti, M.; Kozikowski, A. P.; Johnson, K. M.; Bergmann, J. S. Bioorg. Med. Chem. Lett. 1994, 4, 303.
24. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
25. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
26. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
27. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
28. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
29. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
30. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
31. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
32. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
33. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
34. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
35. For recent advances in tropane alkaloid synthesis, see: (a) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818. (b) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (c) Kozikowski, A. P.; Xiang, L.; Tanaka, J.; Bergman, J. S.; Johnson, K. M. Med. Chem. Res. 1991, 1, 312. (d) Justice, D. E.; Malpass, J. R. Tetrahedron Lett. 1995, 36, 4689. (e) Carroll, F. I.; Kotian, P.; Dehgshani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W. Kuhar, M. J. J. Med. Chem. 1995, 38, 379. (f) Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314. (g) Tuffiarello, J. J.; Mullen, G. B.; Tegleer, J. J.; Trybulski, E. J.; Wong, S. C.; Asrof, Ali, S. J Am. Che. Soc. 1979, 101, 2435. (h) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. (i) Davies, H. M. L.; Huby, N. J. S. Tetrahedron Lett. 1992, 33, 6935. (j) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Uiyan, Z.; Yan, L.; Jingyu, S. J. J. Org. Chem. 1992, 57, 3528. (k) Davies, H. M. L. Tetrahedron 1993, 49, 5203. (l) Davies, H. M. L.; Saikali, E.; Huby, N. J. S.; Gilliat, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. J. Med. Chem. 1994, 37, 1262.
36. Johnson, C. R. in Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Eds.; Pergamon: New York, 1984; Vol. 2, Chapter 2.04.
37. (a) Dennis, N.; Katrizky, A. R.; Takeuchi, Y. Angew. Chem., Int. Ed. Engl. 1976, 15, 1.
38. For a review of cycloaddition reactions of heteroaromatic six-membered rings, including oxidopyridinium and oxidopyrilium systems, see: (b) Katritzky, A. R.; Dennis, N. Chem. Rev. 1989, 89, 827-861.
39. This type of transformation has previously been used to convert the homologous pyrones into pyrilium salts: see ref 2j,k.
40. This salt can be crystallized from EtOAc or used directly as a crude reagent in the cycloaddition step.
41. The reductive removal of the sulfone group has previously been described for related bicyclic systems: Pandey, G.; Lakshamaiah, G.; Ghatak, A. Tetrahedron Lett. 1993, 34, 7301.
42. (a) Katrizky, A.; Dennis, N.; Chaillet, M.; Larrieu, C.; Mouhtadi, M. E. J. Chem. Soc., Perkin Trans. 1 1979, 408.
43. (b) Hamaguchi, M; Matsuura, H; Nagai, T. J. Chem. Soc., Chem. Commun. 1982, 263.
44. Approximate frontier orbital coefficients at the reaction centers of these pyridinium betaines were calculated by the PM3 method using the MOPAC program.
45. 6) in the HOMO of the 4-unsubstituted pyridinium salt.
46. Previous attempts to induce asymmetry in simple oxidopyridinium cycloadditions have been based on the introduction of the chiral auxiliary in the dipolarophile, which leads to poor stereofacial selectivity: Takahashi, T; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizume, T. Tetrahedron Asymmetry 1991, 2, 1379.
47. There is a current interest in the preparation of related fused tropanes: Davies, H. M. L.; Matasi, J. J.; Ahmed, G. J. Org. Chem. 1996, 61, 2305.
48. (a) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. Synthesis 1992, 645.
49. (b) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353.
50. Ando, T.; Yamawaki, J.; Kawate, T.; Sumi, S.; Hanafusa, T. Bull. Chem. Soc. Jpn. 1982, 55, 2504.
51. Wender, P. A.; Miller, B. L. in Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: New York, 1993; Vol. 2, pp 27-66.