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Volumn 68, Issue 17, 2003, Pages 6597-6604

α-Phosphono lactone analogues of cytidine and cytosine arabinoside diphosphates: Synthesis via ring closing metathesis

Author keywords

[No Author keywords available]

Indexed keywords

METATHESIS;

EID: 0043011081     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0300136     Document Type: Article
Times cited : (32)

References (51)
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    • note
    • Both a single-crystal diffraction analysis and more recent ENDOR studies suggest that the phosphoryl groups in ADP adopt an extended conformation with a dihedral angle in the C5′-O5′-PO6′ region (-59° or -52°) consistent with a pseudo-chair conformation of a lactone ring.
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    • note
    • The X-ray diffraction data for single crystals of compounds 17 and 26 are available from the Cambridge Crystallographic Data Centre with reference numbers CCDC 197773 and CCDC 197775.
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    • For ring-closure metathesis strategy applications to preparation of unsatuarated γ- and β-lactones see: (a) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654. (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. (c) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H. J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (d) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155. (e) Greer, P. B.; Donaldson, W. A. Tetrahedron Lett. 2000, 41, 3801-3803. (f) Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. (g) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319-2322. (j) Ghosh, A. K.; Lei, H. J. Org. Chem. 2000, 65, 4779-4781. (i) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586.
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    • For ring-closure metathesis strategy applications to preparation of unsatuarated γ- and β-lactones see: (a) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654. (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. (c) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H. J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (d) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155. (e) Greer, P. B.; Donaldson, W. A. Tetrahedron Lett. 2000, 41, 3801-3803. (f) Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. (g) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319-2322. (j) Ghosh, A. K.; Lei, H. J. Org. Chem. 2000, 65, 4779-4781. (i) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586.
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    • For ring-closure metathesis strategy applications to preparation of unsatuarated γ- and β-lactones see: (a) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654. (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. (c) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H. J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (d) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155. (e) Greer, P. B.; Donaldson, W. A. Tetrahedron Lett. 2000, 41, 3801-3803. (f) Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. (g) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319-2322. (j) Ghosh, A. K.; Lei, H. J. Org. Chem. 2000, 65, 4779-4781. (i) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586.
    • (2000) J. Org. Chem. , vol.65 , pp. 2204-2207
    • Furstner, A.1    Thiel, O.R.2    Ackermann, L.3    Schanz, H.J.4    Nolan, S.P.5
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    • For ring-closure metathesis strategy applications to preparation of unsatuarated γ- and β-lactones see: (a) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654. (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. (c) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H. J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (d) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155. (e) Greer, P. B.; Donaldson, W. A. Tetrahedron Lett. 2000, 41, 3801-3803. (f) Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. (g) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319-2322. (j) Ghosh, A. K.; Lei, H. J. Org. Chem. 2000, 65, 4779-4781. (i) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586.
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    • For ring-closure metathesis strategy applications to preparation of unsatuarated γ- and β-lactones see: (a) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654. (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. (c) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H. J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (d) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155. (e) Greer, P. B.; Donaldson, W. A. Tetrahedron Lett. 2000, 41, 3801-3803. (f) Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. (g) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319-2322. (j) Ghosh, A. K.; Lei, H. J. Org. Chem. 2000, 65, 4779-4781. (i) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 3801-3803
    • Greer, P.B.1    Donaldson, W.A.2
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    • 0034639734 scopus 로고    scopus 로고
    • For ring-closure metathesis strategy applications to preparation of unsatuarated γ- and β-lactones see: (a) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654. (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. (c) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H. J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (d) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155. (e) Greer, P. B.; Donaldson, W. A. Tetrahedron Lett. 2000, 41, 3801-3803. (f) Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. (g) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319-2322. (j) Ghosh, A. K.; Lei, H. J. Org. Chem. 2000, 65, 4779-4781. (i) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 1003-1006
    • Ghosh, A.K.1    Bilcer, G.2
  • 41
    • 0034175522 scopus 로고    scopus 로고
    • For ring-closure metathesis strategy applications to preparation of unsatuarated γ- and β-lactones see: (a) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654. (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. (c) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H. J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (d) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155. (e) Greer, P. B.; Donaldson, W. A. Tetrahedron Lett. 2000, 41, 3801-3803. (f) Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. (g) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319-2322. (j) Ghosh, A. K.; Lei, H. J. Org. Chem. 2000, 65, 4779-4781. (i) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 2319-2322
    • Ghosh, A.K.1    Wang, Y.2
  • 42
    • 0034725917 scopus 로고    scopus 로고
    • For ring-closure metathesis strategy applications to preparation of unsatuarated γ- and β-lactones see: (a) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654. (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. (c) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H. J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (d) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155. (e) Greer, P. B.; Donaldson, W. A. Tetrahedron Lett. 2000, 41, 3801-3803. (f) Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. (g) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319-2322. (j) Ghosh, A. K.; Lei, H. J. Org. Chem. 2000, 65, 4779-4781. (i) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586.
    • (2000) J. Org. Chem. , vol.65 , pp. 4779-4781
    • Ghosh, A.K.1    Lei, H.2
  • 43
    • 0034728178 scopus 로고    scopus 로고
    • For ring-closure metathesis strategy applications to preparation of unsatuarated γ- and β-lactones see: (a) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651-4654. (b) Cossy, J.; Bauer, D.; Bellosta, V. Tetrahedron Lett. 1999, 40, 4187-4188. (c) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H. J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (d) Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155. (e) Greer, P. B.; Donaldson, W. A. Tetrahedron Lett. 2000, 41, 3801-3803. (f) Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006. (g) Ghosh, A. K.; Wang, Y. Tetrahedron Lett. 2000, 41, 2319-2322. (j) Ghosh, A. K.; Lei, H. J. Org. Chem. 2000, 65, 4779-4781. (i) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 583-586
    • Ramachandran, P.V.1    Reddy, M.V.R.2    Brown, H.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.