Carbocyclic nucleoside analogs. 1. Concise enantioselective synthesis of functionalized cyclopentanes and formal total synthesis of aristeromycin

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3976-3980

  Boyer, Stephen J ^a   Leahy, James W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARISTEROMYCIN; CYCLOPENTANE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030754466     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970153d     Document Type: Article

References (64)

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14. Recent examples: (d) Martinez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (e) Campbell, J.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602. (f) Csuk, R.; Dorr, P. Tetrahedron 1995, 51, 5789. (g) Vince, R.; Kilama, J.; Pham, P.; Beers, S.; Bowdon, B.; Kieth, K.; Parker, W. Nucleosides Nucleotides 1995, 14, 1703. (h) Nokami, J.; Matsura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (i) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (j) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745.
15. Recent examples: (d) Martinez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (e) Campbell, J.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602. (f) Csuk, R.; Dorr, P. Tetrahedron 1995, 51, 5789. (g) Vince, R.; Kilama, J.; Pham, P.; Beers, S.; Bowdon, B.; Kieth, K.; Parker, W. Nucleosides Nucleotides 1995, 14, 1703. (h) Nokami, J.; Matsura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (i) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (j) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745.
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17. Recent examples: (d) Martinez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (e) Campbell, J.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602. (f) Csuk, R.; Dorr, P. Tetrahedron 1995, 51, 5789. (g) Vince, R.; Kilama, J.; Pham, P.; Beers, S.; Bowdon, B.; Kieth, K.; Parker, W. Nucleosides Nucleotides 1995, 14, 1703. (h) Nokami, J.; Matsura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (i) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (j) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745.
18. Recent examples: (d) Martinez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (e) Campbell, J.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602. (f) Csuk, R.; Dorr, P. Tetrahedron 1995, 51, 5789. (g) Vince, R.; Kilama, J.; Pham, P.; Beers, S.; Bowdon, B.; Kieth, K.; Parker, W. Nucleosides Nucleotides 1995, 14, 1703. (h) Nokami, J.; Matsura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (i) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (j) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745.
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34. Carbocyclic C-nucleosides such as 1 have not been well explored. For some examples, see: (a) Dishington, A. P.; Humber, D. C.; Stoodley, R. J. J. Chem. Soc. Perkin Trans. 1 1993, 57. (b) Kakeno, C.; Katagiri, N.; Nomura, M.; Sato, H. Israel J. Chem. 1991, 31, 247. (c) Sato, M.; Takayama, K.; Kakeno, C. Chem. Pharm. Bull. 1989, 37, 2615. (d) Saksena, A.; Ganguly, A. Tetrahedron Lett. 1981, 22, 5227. (e) Just, G.; Kim, S. Tetrahedron Lett. 1976 1063.
35. Carbocyclic C-nucleosides such as 1 have not been well explored. For some examples, see: (a) Dishington, A. P.; Humber, D. C.; Stoodley, R. J. J. Chem. Soc. Perkin Trans. 1 1993, 57. (b) Kakeno, C.; Katagiri, N.; Nomura, M.; Sato, H. Israel J. Chem. 1991, 31, 247. (c) Sato, M.; Takayama, K.; Kakeno, C. Chem. Pharm. Bull. 1989, 37, 2615. (d) Saksena, A.; Ganguly, A. Tetrahedron Lett. 1981, 22, 5227. (e) Just, G.; Kim, S. Tetrahedron Lett. 1976 1063.
36. Carbocyclic C-nucleosides such as 1 have not been well explored. For some examples, see: (a) Dishington, A. P.; Humber, D. C.; Stoodley, R. J. J. Chem. Soc. Perkin Trans. 1 1993, 57. (b) Kakeno, C.; Katagiri, N.; Nomura, M.; Sato, H. Israel J. Chem. 1991, 31, 247. (c) Sato, M.; Takayama, K.; Kakeno, C. Chem. Pharm. Bull. 1989, 37, 2615. (d) Saksena, A.; Ganguly, A. Tetrahedron Lett. 1981, 22, 5227. (e) Just, G.; Kim, S. Tetrahedron Lett. 1976 1063.
37. Carbocyclic C-nucleosides such as 1 have not been well explored. For some examples, see: (a) Dishington, A. P.; Humber, D. C.; Stoodley, R. J. J. Chem. Soc. Perkin Trans. 1 1993, 57. (b) Kakeno, C.; Katagiri, N.; Nomura, M.; Sato, H. Israel J. Chem. 1991, 31, 247. (c) Sato, M.; Takayama, K.; Kakeno, C. Chem. Pharm. Bull. 1989, 37, 2615. (d) Saksena, A.; Ganguly, A. Tetrahedron Lett. 1981, 22, 5227. (e) Just, G.; Kim, S. Tetrahedron Lett. 1976 1063.
38. Carbocyclic C-nucleosides such as 1 have not been well explored. For some examples, see: (a) Dishington, A. P.; Humber, D. C.; Stoodley, R. J. J. Chem. Soc. Perkin Trans. 1 1993, 57. (b) Kakeno, C.; Katagiri, N.; Nomura, M.; Sato, H. Israel J. Chem. 1991, 31, 247. (c) Sato, M.; Takayama, K.; Kakeno, C. Chem. Pharm. Bull. 1989, 37, 2615. (d) Saksena, A.; Ganguly, A. Tetrahedron Lett. 1981, 22, 5227. (e) Just, G.; Kim, S. Tetrahedron Lett. 1976 1063.
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