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Volumn 62, Issue 6, 1997, Pages 1580-1581

Efficient synthesis of carbovir and its congener via π-allylpalladium complex formation by ring strain-assisted C-N bond cleavage

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCYCLIC NUCLEOSIDE; CARBOVIR;

EID: 0030894463     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962416u     Document Type: Article
Times cited : (26)

References (30)
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    • For recent reviews of the synthesis of carbocyclic nucleosides, see: (a) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (b) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611. For recent syntheses of carbovir, see: (c) Martinez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (d) Trost, B. M.; Stenkamp, D.; Pulley, S. R. Chem. Eur. J. 1995, 1, 568. (e) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (f) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602. (g) Park, K. H.; Rapoport, H. J. Org. Chem. 1994, 59, 394. (h) Handa, S.; Earlam, G. J.; Geary, P. J.; Hawes, J. E.; Phillips, G. T.; Pryce, R. J.; Ryback, G.; Shears, J. H. J. Chem. Soc., Perkin Trans. 1 1994, 1885.
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    • For recent reviews of the synthesis of carbocyclic nucleosides, see: (a) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. (b) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611. For recent syntheses of carbovir, see: (c) Martinez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (d) Trost, B. M.; Stenkamp, D.; Pulley, S. R. Chem. Eur. J. 1995, 1, 568. (e) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523. (f) Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602. (g) Park, K. H.; Rapoport, H. J. Org. Chem. 1994, 59, 394. (h) Handa, S.; Earlam, G. J.; Geary, P. J.; Hawes, J. E.; Phillips, G. T.; Pryce, R. J.; Ryback, G.; Shears, J. H. J. Chem. Soc., Perkin Trans. 1 1994, 1885.
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    • A trace amount (about 5%) of 7-substituted 6-chloropurine derivative was also obtained as a minor product
    • A trace amount (about 5%) of 7-substituted 6-chloropurine derivative was also obtained as a minor product.
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    • Nucleophiles with Allyl-Metal Complexes
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    • For an excellent review concerning the formation of π-allylpalladium complexes and their reactions, see: Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 4, Chapter 3.3, pp 585-661.
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    • Compound 9 (mp 138-139°C) was obtained in 66% yield by the same procedure given for the preparation of 3a
    • Compound 9 (mp 138-139°C) was obtained in 66% yield by the same procedure given for the preparation of 3a.


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