Asymmetric Intramolecular Diels-Alder Cycloadditions of 2-Pyrone-3-Carboxylates and Synthesis of Vitamin D3 a Ring Phosphine Oxide

Bulletin of the Korean Chemical Society

Volumn 19, Issue 9, 1998, Pages 957-961

  Cho, Cheon Gyu ^a   Posner, Gary H ^b  

^a Hanyang University   (South Korea)

^b JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032341787     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (35)

1. (a) Posner, G. H.; Cho, C.-G.; Tizah, E.; Johson, N.; Horst, R. L.; Kobayashi, T.; Okano, T.; Tsugawa, N. J. Org. Chem. 1995, 60, 4617.
2. (b) Posner, G. H.; Johnson, N. J. Org. Chem. 1994, 59, 7855.
3. 3 compounds, see: (c) Norman, A. W.; Nemere, I.; Muralidharan, K. R.; Okamura, W. H. Biochem. Biophys. Res. Comm. 1992, 189, 1450. (d) Nishi, Y.; Abe, S.; Kobayashi, T.; Okano, T.; Tsugawa, N.; Slatopolsky, E.; Brown, A. J.; Dusso, A.; Raisz, L. G. In Vitamin D: Gene Regulation, Structure-Function Analysis, and Clinical Applications; Norman, A. W., Bouilion, R., Thomsasset, R., Eds.; W. de Gruyter: New York, 1991; p 294.
4. 3 compounds, see: (c) Norman, A. W.; Nemere, I.; Muralidharan, K. R.; Okamura, W. H. Biochem. Biophys. Res. Comm. 1992, 189, 1450. (d) Nishi, Y.; Abe, S.; Kobayashi, T.; Okano, T.; Tsugawa, N.; Slatopolsky, E.; Brown, A. J.; Dusso, A.; Raisz, L. G. In Vitamin D: Gene Regulation, Structure-Function Analysis, and Clinical Applications; Norman, A. W., Bouilion, R., Thomsasset, R., Eds.; W. de Gruyter: New York, 1991; p 294.
5. For reviews, see: (a) Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111. (b) Krivta, V.; Fischer, W. Chimia 1993, 47, 3. (c) Posner, G. H. In Stereocontrolled Organic Synthesis-Chemistry for the 21st Century; Trost, B. M.; Beletskaya, I. P., Eds.; Blackwell Scientific Publications: Oxford, U.K., 1994; p 177. (d) Marko, I. E. Organometallic Reagents in Organic Synthesis; Academic Press: New York, 1994; Chapter 2, p 44.
6. For reviews, see: (a) Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111. (b) Krivta, V.; Fischer, W. Chimia 1993, 47, 3. (c) Posner, G. H. In Stereocontrolled Organic Synthesis-Chemistry for the 21st Century; Trost, B. M.; Beletskaya, I. P., Eds.; Blackwell Scientific Publications: Oxford, U.K., 1994; p 177. (d) Marko, I. E. Organometallic Reagents in Organic Synthesis; Academic Press: New York, 1994; Chapter 2, p 44.
7. For reviews, see: (a) Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111. (b) Krivta, V.; Fischer, W. Chimia 1993, 47, 3. (c) Posner, G. H. In Stereocontrolled Organic Synthesis-Chemistry for the 21st Century; Trost, B. M.; Beletskaya, I. P., Eds.; Blackwell Scientific Publications: Oxford, U.K., 1994; p 177. (d) Marko, I. E. Organometallic Reagents in Organic Synthesis; Academic Press: New York, 1994; Chapter 2, p 44.
8. For reviews, see: (a) Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111. (b) Krivta, V.; Fischer, W. Chimia 1993, 47, 3. (c) Posner, G. H. In Stereocontrolled Organic Synthesis-Chemistry for the 21st Century; Trost, B. M.; Beletskaya, I. P., Eds.; Blackwell Scientific Publications: Oxford, U.K., 1994; p 177. (d) Marko, I. E. Organometallic Reagents in Organic Synthesis; Academic Press: New York, 1994; Chapter 2, p 44.
9. For some of the recent examples on asymmetric cycloadditions, see: (a) Kozman, S.; Rawal, V. J. Am. Chem. Soc. 1997, 119, 7165. (b) Gilbertson, S. R.; Lopez, O. D. J. Am. Chem. Soc. 1997, 119, 3399. (c) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 2950.
10. For some of the recent examples on asymmetric cycloadditions, see: (a) Kozman, S.; Rawal, V. J. Am. Chem. Soc. 1997, 119, 7165. (b) Gilbertson, S. R.; Lopez, O. D. J. Am. Chem. Soc. 1997, 119, 3399. (c) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 2950.
11. For some of the recent examples on asymmetric cycloadditions, see: (a) Kozman, S.; Rawal, V. J. Am. Chem. Soc. 1997, 119, 7165. (b) Gilbertson, S. R.; Lopez, O. D. J. Am. Chem. Soc. 1997, 119, 3399. (c) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 2950.
12. For general review on intramolecular cycloadditions, see: (a) Roush, W. R. In Advances in Cycloadditions; Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Marwoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH publishers: 1994; Chapter 9, p 413. (c) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions, Springer-Verlag: New York, 1984. (d) Taschner, M. Organic Synthesis: Theory and Application, JAI Press, 1989, vol 1, p 1. (e) Caruthers, W. Cycloaddition reactions in Organic Synthesis; Pergamon: New York, 1990. (i) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023.
13. For general review on intramolecular cycloadditions, see: (a) Roush, W. R. In Advances in Cycloadditions; Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Marwoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH publishers: 1994; Chapter 9, p 413. (c) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions, Springer-Verlag: New York, 1984. (d) Taschner, M. Organic Synthesis: Theory and Application, JAI Press, 1989, vol 1, p 1. (e) Caruthers, W. Cycloaddition reactions in Organic Synthesis; Pergamon: New York, 1990. (i) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023.
14. For general review on intramolecular cycloadditions, see: (a) Roush, W. R. In Advances in Cycloadditions; Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Marwoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH publishers: 1994; Chapter 9, p 413. (c) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions, Springer-Verlag: New York, 1984. (d) Taschner, M. Organic Synthesis: Theory and Application, JAI Press, 1989, vol 1, p 1. (e) Caruthers, W. Cycloaddition reactions in Organic Synthesis; Pergamon: New York, 1990. (i) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023.
15. For general review on intramolecular cycloadditions, see: (a) Roush, W. R. In Advances in Cycloadditions; Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Marwoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH publishers: 1994; Chapter 9, p 413. (c) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions, Springer-Verlag: New York, 1984. (d) Taschner, M. Organic Synthesis: Theory and Application, JAI Press, 1989, vol 1, p 1. (e) Caruthers, W. Cycloaddition reactions in Organic Synthesis; Pergamon: New York, 1990. (i) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023.
16. For general review on intramolecular cycloadditions, see: (a) Roush, W. R. In Advances in Cycloadditions; Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Marwoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH publishers: 1994; Chapter 9, p 413. (c) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions, Springer-Verlag: New York, 1984. (d) Taschner, M. Organic Synthesis: Theory and Application, JAI Press, 1989, vol 1, p 1. (e) Caruthers, W. Cycloaddition reactions in Organic Synthesis; Pergamon: New York, 1990. (i) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023.
17. For general review on intramolecular cycloadditions, see: (a) Roush, W. R. In Advances in Cycloadditions; Curran, D. P., Ed.; JAI: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Marwoka, K.; Yamamoto, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH publishers: 1994; Chapter 9, p 413. (c) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions, Springer-Verlag: New York, 1984. (d) Taschner, M. Organic Synthesis: Theory and Application, JAI Press, 1989, vol 1, p 1. (e) Caruthers, W. Cycloaddition reactions in Organic Synthesis; Pergamon: New York, 1990. (i) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023.
18. Use of chiral thiazolidinethione for asymmetric cycloaddition: (a) Evans, D. A.; Chapman, K. T.; Bisaha, J. Tetrahedron Lett. 1984, 25, 4071. (b) Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 2169.
19. Use of chiral thiazolidinethione for asymmetric cycloaddition: (a) Evans, D. A.; Chapman, K. T.; Bisaha, J. Tetrahedron Lett. 1984, 25, 4071. (b) Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1993, 34, 2169.
20. Vinyl silane for IMDA: (a) Sieburth, S. M.; Fensterbank, L. J. Org. Chem. 1992, 57, 5279-5281. (b) Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446.
21. Vinyl silane for IMDA: (a) Sieburth, S. M.; Fensterbank, L. J. Org. Chem. 1992, 57, 5279-5281. (b) Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446.
22. Posner, G. H.; Nelson, T. D.; Kinter, C. M.; Johnson, N. J. Org. Chem. 1992, 57, 4083.
23. For use of silaketals as tethered dienophiles for IMDA, see: (a) Shea, K. J.; Gauthier, D. R., Jr. Tetrahedron Lett. 1994, 35, 7311. (b) Garner, P. P.; Cox, P. B.; Klippenstein, S. J.; Young, W. J.; McConville, D. B. J. Org. Chem. 1994, 59, 6510. (c) Colombier, C.; Skrydstrup, T.; Beau, J.-M. Tetrahedron Lett. 1994, 35, 8167. (d) Fairbanks, A.; Perrin, E.; Sinay, P. Synlett 1996, 679.
24. For use of silaketals as tethered dienophiles for IMDA, see: (a) Shea, K. J.; Gauthier, D. R., Jr. Tetrahedron Lett. 1994, 35, 7311. (b) Garner, P. P.; Cox, P. B.; Klippenstein, S. J.; Young, W. J.; McConville, D. B. J. Org. Chem. 1994, 59, 6510. (c) Colombier, C.; Skrydstrup, T.; Beau, J.-M. Tetrahedron Lett. 1994, 35, 8167. (d) Fairbanks, A.; Perrin, E.; Sinay, P. Synlett 1996, 679.
25. For use of silaketals as tethered dienophiles for IMDA, see: (a) Shea, K. J.; Gauthier, D. R., Jr. Tetrahedron Lett. 1994, 35, 7311. (b) Garner, P. P.; Cox, P. B.; Klippenstein, S. J.; Young, W. J.; McConville, D. B. J. Org. Chem. 1994, 59, 6510. (c) Colombier, C.; Skrydstrup, T.; Beau, J.-M. Tetrahedron Lett. 1994, 35, 8167. (d) Fairbanks, A.; Perrin, E.; Sinay, P. Synlett 1996, 679.
26. For use of silaketals as tethered dienophiles for IMDA, see: (a) Shea, K. J.; Gauthier, D. R., Jr. Tetrahedron Lett. 1994, 35, 7311. (b) Garner, P. P.; Cox, P. B.; Klippenstein, S. J.; Young, W. J.; McConville, D. B. J. Org. Chem. 1994, 59, 6510. (c) Colombier, C.; Skrydstrup, T.; Beau, J.-M. Tetrahedron Lett. 1994, 35, 8167. (d) Fairbanks, A.; Perrin, E.; Sinay, P. Synlett 1996, 679.
27. The high pressure Diels-Alder cycloadditions of systems 3, 4, 7 proceeded in a concerted manner to provide different stereochemical outcomes. Details will be published elsewhere.
28. For the synthesis of the system 7, see: ref 1(a).
29. For the detailed stereochemical assignments, see: ref 1(a).
30. Some of the recent examples: (a) Storer, J. W.; raimondi, L.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 96753. (b) Linkert, F.; Laschat, S.; Kotila, S.; Fox, T. Tetrahedron 1996, 52, 955. (c) Leung, S.-W.; Singleton, D. J. Org. Chem. 1997, 62, 1955.
31. Some of the recent examples: (a) Storer, J. W.; raimondi, L.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 96753. (b) Linkert, F.; Laschat, S.; Kotila, S.; Fox, T. Tetrahedron 1996, 52, 955. (c) Leung, S.-W.; Singleton, D. J. Org. Chem. 1997, 62, 1955.
32. Some of the recent examples: (a) Storer, J. W.; raimondi, L.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 96753. (b) Linkert, F.; Laschat, S.; Kotila, S.; Fox, T. Tetrahedron 1996, 52, 955. (c) Leung, S.-W.; Singleton, D. J. Org. Chem. 1997, 62, 1955.
33. Mandai, T.; Imaji, M.; Takada, H.; Kawata, M.; Nokami, J.; Tsuji, J. J. Org. Chem. 1989, 54, 5395.
34. Posner, G. H.; Crouch, R. D.; Kinter, C. M.; Carry, J.-C. J. Org. Chem. 1991, 56, 6981.
35. Lythgoe, B.; Moran, T. A.; Nambudiry, M. E. N.; Tideswell, J.; Wright, P. W. J. Chem. Soc. Perkin Trans. I 1978, 590.