Visible Light Initiated Photosensitized Electron Transfer Cyclizations of Aldehydes and Ketones to Tethered αβ-Unsaturated Esters: Stereoselective Synthesis of Optically Pure C-Furanosides

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5966-5973

  Pandey, Ganesh ^a   Hajra, Saumen ^a   Ghorai, Manas K ^a   Ravi Kumar, K ^b  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000020739     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9702812     Document Type: Article

References (50)

1. (a) Sowell, C. G.; Wolin, R. L.; Little, R. D. Tetrahedron Lett. 1990, 31, 485.
2. (b) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, K.; Kato, Y.; Kurozumi, S.; Noyori, R. Tetrahedron 1990, 46, 6689.
3. (c) Enholm, E. J.; Trivellas, A. J. Am. Chem. Soc. 1989, 111, 6463.
4. (d) Enholm, E. J.; Satici, H.; Trivellas, A. J. Org. Chem. 1989, 54, 5841.
5. Corey, E. J.; Pyne, S. G. Tetrahedron Lett. 1983, 24, 2821.
6. (a) Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063.
7. (b) Shim, S. C.; Hwang, J. T.; Kang, H. Y.; Chang, M. H. Tetrahedron Lett. 1990, 31, 4765.
8. (c) Inokuchi, T.; Kawafuchi, H.; Torri, S. J. Org. Chem. 1991, 56, 4983.
9. Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939.
10. (a) Stork, G.; Malhotra, S.; Thompson, H.; Uchibayashi, M. J. Am. Chem. Soc. 1965, 87, 1148.
11. (b) Pradhan, S. K.; Radhakrishnan, T. V.; Subramanian, R. J. Org. Chem. 1976, 41, 1943.
12. (c) Pradhan, S. K.; Kadam, S. R.; Kolhe, J. N.; Radhakrishnan, T. V.; Sohani, S. V.; Thaker, V. B. J. Org. Chem. 1981, 46, 2622.
13. Little, R. D.; Fox, D. P.; Hijfte, L. V.; Dannecker, R.; Sowell, G.; Wolin, R. L.; Moens, L.; Baizer, M. M. J. Org. Chem. 1988, 53, 2287.
14. (a) Belotti, D.; Cossy, J.; Pete, J. P.; Portella, C. Tetrahedron Lett. 1985, 26, 4591.
15. (b) Cossy, J.; Pete, J. P.; Portella, C. Tetrahedron Lett. 1989, 30, 7361.
16. (a) Pandey, G.; Hajra, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 1169.
17. (b) Pandey, G.; Hajra, S.; Ghorai, M. K.; Ravi Kumar, K. J. Am. Chem. Soc., in press.
18. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
19. Mattes, S. L.; Farid, S. Org. Photochem. 1983, 6, 223.
20. et value are only approximate; however, it agrees generally quite well with experimental result.
21. Calvert, J. G.; Pitts, J. N. Photochemistry; Wiley: New York, 1966; p 736.
22. At this stage we are not sure of the exact mechanistic detail about this observation; however, the effect of aqueous solvent might be pointed out in this regard.
23. Reviews: (a) Suhadolink, R. J. Nucleoside Antibiotics; Wiley-Interscience: New York, 1970; p 354. (b) Daves, G. D., Jr.; Cheng, C. C. Progr. Med. Chem. 1976, 13, 303. (c) Hanessian, S.; Pernet, A. G. Adv. Carbohydr. Chem. Biochem. 1976, 33, 111.
24. Reviews: (a) Suhadolink, R. J. Nucleoside Antibiotics; Wiley-Interscience: New York, 1970; p 354. (b) Daves, G. D., Jr.; Cheng, C. C. Progr. Med. Chem. 1976, 13, 303. (c) Hanessian, S.; Pernet, A. G. Adv. Carbohydr. Chem. Biochem. 1976, 33, 111.
25. Reviews: (a) Suhadolink, R. J. Nucleoside Antibiotics; Wiley-Interscience: New York, 1970; p 354. (b) Daves, G. D., Jr.; Cheng, C. C. Progr. Med. Chem. 1976, 13, 303. (c) Hanessian, S.; Pernet, A. G. Adv. Carbohydr. Chem. Biochem. 1976, 33, 111.
26. (a) Hosova, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004.
27. (b) Cha, J. K.; Christ, W. J.; Finan, J. M.; Fujioka, H.; Kishi, Y.; Klein, L. L.; Ko, S. S.; Leder, J.; McWhorter, W. W., Jr.; Pfaff, K.-P.; Yonaga, M.; Uemura, D.; Hirata, Y. J. Am. Chem. Soc. 1982, 104, 7369.
28. (a) Hanessian, S.; Pernet, A. G. Adv. Carbohydr. Chem. Biochem. 1976, 33, 111.
29. (b) Daves, G. D.; Cheng, C. C. Prog. Med. Chem. 1976, 13, 303.
30. (a) Barrett, A. G. M.; Broughton, H. B. J. Org. Chem. 1984, 49, 3673.
31. (b) Gonzalez, M. S. P.; Aciego, R. M. D.; Herrera, F. J. L. Tetrahedron 1988, 44, 3715.
32. (a) Araki, Y.; Endo, T.; Tanaji, M.; Nagasawa, J.; Ishido, Y. Tetrahedron Lett. 1988, 29, 351.
33. (b) Barton, D. H. R.; Ramesh, M. J. Am. Chem. Soc. 1990, 112, 891.
34. (a) Togo, H.; Fujii, M.; Ikuma, T.; Yokoyama, M. Tetrahedron Lett. 1991, 32, 6559.
35. (b) Togo, H.; Aoki, M.; Yokoyama, M. Tetrahedron Lett. 1991, 32, 6559.
36. (a) Inuoe, T.; Kuwajima, I. J. Chem. Soc., Chem. Commun. 1980, 251.
37. (b) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289.
38. (a) Noyori, R.; Sato, T.; Hayakawa, Y. J. Am. Chem. Soc. 1978, 100, 2561.
39. (b) Sato, T.; Ito, R.; Hayakawa, Y.; Noyori, R. Tetrahedron Lett. 1978, 1829.
40. Just, G.; Liak, T. J.; Lim, M.; Potvin, P.; Tsantrizos, Y. S. Can. J. Chem. 1980, 58, 2024.
41. (a) Lee, E.; Tae, J. S.; Lee, C.; Park, C. M. Tetrahedron Lett. 1993, 34, 4831.
42. (b) Lee, E.; Park, C. M. J. Chem. Soc., Chem. Commun. 1994, 293.
43. Al-Hakim, A. H.; Haines, A. H.; Morley, C. Synthesis 1985, 207.
44. Winterfeldt, E.; Preuss, H. Chem. Ber. 1966, 99, 450.
45. Tsuzuki, K.; Nakajima, Y.; Watanabe, T.; Yanagiya, M.; Matsumoto, T. Tetrahedron Lett. 1978, 989.
46. In our present experimental conditions, we always got cyclized product 40 in desilylated form.
47. Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.
48. Ehrlenmeyer, E. Biochem. Z. 1915, 68, 351.
49. Fujita, K.; Nakai, H.; Kobayashi, S.; Inoue, K.; Nujima, S.; Ohno, M. Tetrahedron Lett. 1982, 23, 3507.
50. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.