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Volumn , Issue 2, 2005, Pages 231-234

A flexible carbanionic approach to protected trans-(2R,3S)-2-substituted 3-aminopyrrolidines: Application to the asymmetric synthesis of (+)-absouline

Author keywords

Additions; Asymmetric synthesis; Carbanions; Pyrrolidine; Reductive lithiation

Indexed keywords

1 AMINOPYRROLIZIDINE ALKALOID; 2 LITHIOPIPERIDINE DERIVATIVE; 3 AMINO 2 THIOPHENYLPYRROLIDINE; ABSOULINE; ANION; ISOABSOULINE; LABURNAMINE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; PYRROLIZIDINE ALKALOID; SULFIDE; UNCLASSIFIED DRUG;

EID: 13844265719     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837194     Document Type: Article
Times cited : (20)

References (64)
  • 1
    • 0028157516 scopus 로고
    • For reviews involving the generation and application of α-lithioamines, see: (a) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
    • (1994) Tetrahedron , vol.50 , pp. 2297
    • Gant, T.G.1    Meyers, A.I.2
  • 8
    • 0022382945 scopus 로고
    • For representative approaches to optically active α- lithiopyrrolidines and α-lithiopiperidines, see: (a) Meyers, A. I.; Dickman, D. A.; Bailey, T. R. J. Am. Chem. Soc. 1985, 107, 7974.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 7974
    • Meyers, A.I.1    Dickman, D.A.2    Bailey, T.R.3
  • 18
    • 0344927927 scopus 로고    scopus 로고
    • For chiral non-racemic synthetic equivalents to synthon 2b (X = OH, OP), see: (a) Huang, P.-Q.; Wu,T.-J.;Ruan, Y.-P. Org. Lett. 2003, 5, 4341.
    • (2003) Org. Lett. , vol.5 , pp. 4341
    • Huang, P.-Q.1    Wu, T.-J.2    Ruan, Y.-P.3
  • 24
    • 0026030769 scopus 로고
    • (b) Drugs Future 1991, 16, 95.
    • (1991) Drugs Future , vol.16 , pp. 95
  • 34
  • 35
    • 0032546067 scopus 로고    scopus 로고
    • (b) For an approach to optically active 1-aminopyrrolizidin-3-one derivative, see: Langlois, N.; Radom, M.-O. Tetrahedron Lett. 1998, 39, 857.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 857
    • Langlois, N.1    Radom, M.-O.2
  • 39
    • 13844297208 scopus 로고    scopus 로고
    • Ref. 13
    • Ref. 13.
  • 59
    • 13844281890 scopus 로고    scopus 로고
    • note
    • All new compounds gave satisfactory analytical and spectral data.
  • 60
    • 13844271595 scopus 로고    scopus 로고
    • note
    • +: 379.2234; found: 379.2233.
  • 63
    • 13844298425 scopus 로고    scopus 로고
    • note
    • 13C NMR spectral data of 1-aminopyrrolizidine and its derivatives (13,10a 14,10a,12 4,11,12 and 511,12), some differences exist from one to the other. This may be due to conformational isomerism and/or H-bond formation in the 1-aminopyrrolizidine ring system. In addition, these molecules were shown to be labile.
  • 64
    • 13844272746 scopus 로고    scopus 로고
    • note
    • We thank Dr. C. Poupat (Institut de Chimie des Substances Naturelles, CNRS, France) for sending us a sample of natural absouline.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.