메뉴 건너뛰기




Volumn 54, Issue 35, 1998, Pages 10457-10468

Synthesis of indolizidines (-)-195B, (-)-223AB and (-)-239AB: (2S,5R)- l-[(benzyloxy)carbonyl]-2-methoxycarbonyl-5-(4pentenyl)pyrrolidine as a versatile chiral building block

Author keywords

[No Author keywords available]

Indexed keywords

1 [(BENZYLOXY)CARBONYL] 2 METHOXYCARBONYL 5 (4 PENTENYL)PYRROLIDINE; 1 [(BENZYLOXY)CARBONYL] 2 METHOXYCARBONYL 5 (PENT 4 ENYL)PYRROLIDINE; 3 BUTYL 5 (3 HYDROXYPROPYL)OCTAHYDROINDOLIZIDINE; 3 BUTYL 5 METHYLOCTAHYDROINDOLIZIDINE; 3 BUTYL 5 PROPYLOCTAHYDROINDOLIZIDINE; COPPER DERIVATIVE; INDOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032572841     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00498-0     Document Type: Article
Times cited : (35)

References (27)
  • 1
    • 0010440657 scopus 로고    scopus 로고
    • note
    • 1. This paper is dedicated to Professor Sigeru Torii on the occasion of his retirement from Okayama University.
  • 4
    • 0021919096 scopus 로고
    • 4 Royer, J.; Husson, H.-P. Tetrahedron Lett., 1985, 26, 1515-1518; Taber, D. F.; Deker, P. B.; Silverberg, L. J. J. Org. Chem., 1992, 57, 5991-5994; Fleurant, A.; Célérier, J.-P.; Lhommet, G. Tetrahedron: Asymmetry, 1993, 4, 1429-1430; Pilli, R. A.; Dias, C.; Maldaner, A. O. J. Org. Chem., 1995, 60, 717-722 and references cited therein.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 1515-1518
    • Royer, J.1    Husson, H.-P.2
  • 5
    • 0010482708 scopus 로고
    • 4 Royer, J.; Husson, H.-P. Tetrahedron Lett., 1985, 26, 1515-1518; Taber, D. F.; Deker, P. B.; Silverberg, L. J. J. Org. Chem., 1992, 57, 5991-5994; Fleurant, A.; Célérier, J.-P.; Lhommet, G. Tetrahedron: Asymmetry, 1993, 4, 1429-1430; Pilli, R. A.; Dias, C.; Maldaner, A. O. J. Org. Chem., 1995, 60, 717-722 and references cited therein.
    • (1992) J. Org. Chem. , vol.57 , pp. 5991-5994
    • Taber, D.F.1    Deker, P.B.2    Silverberg, L.J.3
  • 6
    • 0027171786 scopus 로고
    • 4 Royer, J.; Husson, H.-P. Tetrahedron Lett., 1985, 26, 1515-1518; Taber, D. F.; Deker, P. B.; Silverberg, L. J. J. Org. Chem., 1992, 57, 5991-5994; Fleurant, A.; Célérier, J.-P.; Lhommet, G. Tetrahedron: Asymmetry, 1993, 4, 1429-1430; Pilli, R. A.; Dias, C.; Maldaner, A. O. J. Org. Chem., 1995, 60, 717-722 and references cited therein.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1429-1430
    • Fleurant, A.1    Célérier, J.-P.2    Lhommet, G.3
  • 7
    • 0028840773 scopus 로고
    • 4 Royer, J.; Husson, H.-P. Tetrahedron Lett., 1985, 26, 1515-1518; Taber, D. F.; Deker, P. B.; Silverberg, L. J. J. Org. Chem., 1992, 57, 5991-5994; Fleurant, A.; Célérier, J.-P.; Lhommet, G. Tetrahedron: Asymmetry, 1993, 4, 1429-1430; Pilli, R. A.; Dias, C.; Maldaner, A. O. J. Org. Chem., 1995, 60, 717-722 and references cited therein.
    • (1995) J. Org. Chem. , vol.60 , pp. 717-722
    • Pilli, R.A.1    Dias, C.2    Maldaner, A.O.3
  • 10
    • 0001542017 scopus 로고
    • 7. Stevens, R. V. Acc. Chem. Res., 1984, 17, 289-296; Nakagawa, Y.; Stevens, R. V. J. Org. Chem., 1988, 53, 1871-1873; Saliou, C.; Fleurant, A.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 1991, 32, 3365-3368; Takahat, H.; Bandoh, H.; Momose, T. Tetrahedron, 1993, 49, 11205-11212.
    • (1984) Acc. Chem. Res. , vol.17 , pp. 289-296
    • Stevens, R.V.1
  • 11
    • 0023884620 scopus 로고
    • 7. Stevens, R. V. Acc. Chem. Res., 1984, 17, 289-296; Nakagawa, Y.; Stevens, R. V. J. Org. Chem., 1988, 53, 1871-1873; Saliou, C.; Fleurant, A.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 1991, 32, 3365-3368; Takahat, H.; Bandoh, H.; Momose, T. Tetrahedron, 1993, 49, 11205-11212.
    • (1988) J. Org. Chem. , vol.53 , pp. 1871-1873
    • Nakagawa, Y.1    Stevens, R.V.2
  • 12
    • 0025872902 scopus 로고
    • 7. Stevens, R. V. Acc. Chem. Res., 1984, 17, 289-296; Nakagawa, Y.; Stevens, R. V. J. Org. Chem., 1988, 53, 1871-1873; Saliou, C.; Fleurant, A.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 1991, 32, 3365-3368; Takahat, H.; Bandoh, H.; Momose, T. Tetrahedron, 1993, 49, 11205-11212.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3365-3368
    • Saliou, C.1    Fleurant, A.2    Célérier, J.-P.3    Lhommet, G.4
  • 13
    • 0027380329 scopus 로고
    • 7. Stevens, R. V. Acc. Chem. Res., 1984, 17, 289-296; Nakagawa, Y.; Stevens, R. V. J. Org. Chem., 1988, 53, 1871-1873; Saliou, C.; Fleurant, A.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 1991, 32, 3365-3368; Takahat, H.; Bandoh, H.; Momose, T. Tetrahedron, 1993, 49, 11205-11212.
    • (1993) Tetrahedron , vol.49 , pp. 11205-11212
    • Takahat, H.1    Bandoh, H.2    Momose, T.3
  • 16
    • 0000219321 scopus 로고
    • 10. Shono, T.; Matsumura, Y.; Tsubata, K. Org. Synth., 1985, 63, 206-213; Shono, T.; Matsumura, Y.; Kanazawa, T.; Habuka, M.; Unchida, K.; Toyoda, K. J. Chem. Research. (S), 1984, 320-321; (M) 1984, 2876-2889. Electrolysis of 4 under the conditions described by T. Shono et al resulted in a statistical mixture of the two regioisomers. α-Electromethoxylation of 4 was then examined at different temperatures and current densities. The best results were obtained when the electrolysis was conducted at low temperature (-20 to -5°C).
    • (1985) Org. Synth. , vol.63 , pp. 206-213
    • Shono, T.1    Matsumura, Y.2    Tsubata, K.3
  • 17
    • 0002499661 scopus 로고
    • 10. Shono, T.; Matsumura, Y.; Tsubata, K. Org. Synth., 1985, 63, 206-213; Shono, T.; Matsumura, Y.; Kanazawa, T.; Habuka, M.; Unchida, K.; Toyoda, K. J. Chem. Research. (S), 1984, 320-321; (M) 1984, 2876-2889. Electrolysis of 4 under the conditions described by T. Shono et al resulted in a statistical mixture of the two regioisomers. α-Electromethoxylation of 4 was then examined at different temperatures and current densities. The best results were obtained when the electrolysis was conducted at low temperature (-20 to -5°C).
    • (1984) J. Chem. Research. (S) , pp. 320-321
    • Shono, T.1    Matsumura, Y.2    Kanazawa, T.3    Habuka, M.4    Unchida, K.5    Toyoda, K.6
  • 18
    • 0010483736 scopus 로고
    • 10. Shono, T.; Matsumura, Y.; Tsubata, K. Org. Synth., 1985, 63, 206-213; Shono, T.; Matsumura, Y.; Kanazawa, T.; Habuka, M.; Unchida, K.; Toyoda, K. J. Chem. Research. (S), 1984, 320-321; (M) 1984, 2876-2889. Electrolysis of 4 under the conditions described by T. Shono et al resulted in a statistical mixture of the two regioisomers. α-Electromethoxylation of 4 was then examined at different temperatures and current densities. The best results were obtained when the electrolysis was conducted at low temperature (-20 to -5°C).
    • (1984) J. Chem. Research. (M) , pp. 2876-2889
  • 20
    • 0010486067 scopus 로고    scopus 로고
    • note
    • 12. Tolylsulfonate 7 may evolve into oxazolidinone 19, when is left pure at room temperature or during evaporation of solvents at temperature higher than 40°C. (figure presented)
  • 24
    • 0010444435 scopus 로고    scopus 로고
    • note
    • D -44 (c = 1, hexane)} see reference 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.