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Volumn , Issue 4, 2004, Pages 684-687

HIV protease inhibitors part 2: [3+2] Cycloaddition, isomerization; and ring expansion en route to 4,5-substituted cyclohexenones

Author keywords

Cyclohexenone; Cyclopentene; HIV protease inhibitor; Ring expansion; 3+2 cycloaddition

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; INDINAVIR; PROTEINASE INHIBITOR;

EID: 1642348428     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815439     Document Type: Article
Times cited : (6)

References (26)
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    • Use of propiolate trialkylester could have avoided obtaining this by-product but the large scale synthesis of these compounds was considered difficult. See for example: Baldwin, J. E.; Pritchard, G. J.; Rathmell, R. E. Synth. Commun. 2000, 30, 3833.
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    • For the procedures used to synthesize 17 see: (a) Brimble, M. A.; Edmonds, M. K.; Williams, G. M. Tetrahedron 1992, 48, 6455. (b) Marshall, J. A. ; Andrews, R. C.; Lebioda, L. J. Org. Chem. 1987, 52, 2378.
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  • 14
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    • For the procedures used to synthesize 17 see: (a) Brimble, M. A.; Edmonds, M. K.; Williams, G. M. Tetrahedron 1992, 48, 6455. (b) Marshall, J. A. ; Andrews, R. C.; Lebioda, L. J. Org. Chem. 1987, 52, 2378.
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    • This type of compound can be obtained by olefin metathesis but the high dilution of these reaction is not compatible with the scale of reaction envisioned in this synthesis, see: Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4651
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    • CCDC No. 217035 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ conts/retrieving.html (or from the CCDC 12 Union Road Cambridge CB2 1EZ UK; fax:+44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk)
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    • An other approach was attempted using literature precedent, see: (a) Hanessian, S.; Haeil, P.; Rui-Yang, Y. Synlett 1997, 353. (b) Nicoll-Griffith,D. A.; Weiler, L. Tetrahedron 1991, 47, 2733.
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    • An other approach was attempted using literature precedent, see: (a) Hanessian, S.; Haeil, P.; Rui-Yang, Y. Synlett 1997, 353. (b) Nicoll-Griffith,D. A.; Weiler, L. Tetrahedron 1991, 47, 2733.
    • (1991) Tetrahedron , vol.47 , pp. 2733
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    • N,N-Dibenzyl amine was considered to be a reasonable solution. For an excellent review on N,N-dibenzylamino compounds see: Reetz, M. T. Chem. Rev. 1999, 99, 1121.
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    • note
    • The reaction of 14 with oxazolidinone 4 was non-selective. Adduct 28 was obtained as a 1:1 mixture of trans-isomers.
  • 25
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    • note
    • The direct reduction of allylic sulfone 28 gave a mixture of alkenes.


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