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Volumn 46, Issue 30, 2007, Pages 5734-5736

A practical synthesis of (-)-oseltamivir

Author keywords

Antiviral agents; Diels Alder reaction; Domino reactions; Lactones; Rearrangement

Indexed keywords

PHOSPHATES; PURIFICATION; SYNTHESIS (CHEMICAL);

EID: 34547445036     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701754     Document Type: Article
Times cited : (174)

References (31)
  • 12
    • 34547416096 scopus 로고    scopus 로고
    • for a recent review of syntheses of oseltamivir, see
    • j) for a recent review of syntheses of oseltamivir, see: V. Farina, J. D. Brown, Angew. Chem. 2006, 118, 7488;
    • (2006) Angew. Chem , vol.118 , pp. 7488
    • Farina, V.1    Brown, J.D.2
  • 13
    • 33751254092 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7330.
    • (2006) Chem. Int. Ed , vol.45 , pp. 7330
    • Angew1
  • 16
    • 0037037936 scopus 로고    scopus 로고
    • For enantioselective Diels-Alder reactions of dihydropyridines, see: a
    • For enantioselective Diels-Alder reactions of dihydropyridines, see: a) N. Takenaka, Y. Huang, V. H. Rawal, Tetrahedron 2002, 58, 8299;
    • (2002) Tetrahedron , vol.58 , pp. 8299
    • Takenaka, N.1    Huang, Y.2    Rawal, V.H.3
  • 21
    • 0000188220 scopus 로고    scopus 로고
    • for diastereoselective Diels-Alder reactions of chiral acrylic acid derivatives with dihydropyridines, see: f C. Kouklovsky, A. Pouilhès, Y. Langlois, J. Am. Chem. Soc. 1990, 112, 6672;
    • for diastereoselective Diels-Alder reactions of chiral acrylic acid derivatives with dihydropyridines, see: f) C. Kouklovsky, A. Pouilhès, Y. Langlois, J. Am. Chem. Soc. 1990, 112, 6672;
  • 25
    • 34547491300 scopus 로고    scopus 로고
    • The main by-product was benzyl (5-formylcyclohexa-2,4-dienyl) methylcarbamate, which was isolated as the corresponding alcohol after reduction of the crude mixture of aldehydes (see the Supporting Information). The exo isomer was not detected.
    • The main by-product was benzyl (5-formylcyclohexa-2,4-dienyl) methylcarbamate, which was isolated as the corresponding alcohol after reduction of the crude mixture of aldehydes (see the Supporting Information). The exo isomer was not detected.
  • 29
    • 34547480919 scopus 로고    scopus 로고
    • In an experiment with 4.5 g of 14, 93, of the RuO 2·n H2O used could be recovered by the addition of isopropanol to the reaction mixture followed by filtration. The recovered material could be reused and showed no sign of deterioration (see the Supporting Information, Oxone could also be used as a cooxidant 90% over 2 steps, Quite recently, we found that n-propyl acetate, a safer solvent than dichloroethane, could be used with similar results
    • 2O used could be recovered by the addition of isopropanol to the reaction mixture followed by filtration. The recovered material could be reused and showed no sign of deterioration (see the Supporting Information). Oxone could also be used as a cooxidant (90% over 2 steps). Quite recently, we found that n-propyl acetate, a safer solvent than dichloroethane, could be used with similar results.
  • 31
    • 34547406755 scopus 로고    scopus 로고
    • The relatively low yield of 20 was attributed to the concomitant formation of oxazolidinone 22. The mixture was readily separable by chromatography on silica gel. (Chemical Equation Presented)
    • The relatively low yield of 20 was attributed to the concomitant formation of oxazolidinone 22. The mixture was readily separable by chromatography on silica gel. (Chemical Equation Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.