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Volumn 9, Issue 13, 1998, Pages 2201-2205

Asymmetric synthesis of functionalized piperidine derivatives: Synthesis of (S)-anatabine

Author keywords

[No Author keywords available]

Indexed keywords

ANATABINE; PIPERIDINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032479484     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00225-0     Document Type: Article
Times cited : (39)

References (46)
  • 1
    • 0001662681 scopus 로고    scopus 로고
    • Synthetic Methods 48. For paper 47 see
    • Synthetic Methods 48. For paper 47 see: Ghera, E.; Yechezkel, T.; Hassner, A. J. Org. Chem. 1996, 61, 4959-4966.
    • (1996) J. Org. Chem. , vol.61 , pp. 4959-4966
    • Ghera, E.1    Yechezkel, T.2    Hassner, A.3
  • 27
    • 0011383755 scopus 로고
    • Refluxing (Z)-4-chloro-but-2-en-1-ol with sodium salt of sulfinic acid in MeOH for 8 h afforded 1 in 60% yield. (Z)-4-Chloro-but-2-en-1-ol was prepared from cis-but-2-en-1-ol following the procedure of
    • Refluxing (Z)-4-chloro-but-2-en-1-ol with sodium salt of sulfinic acid in MeOH for 8 h afforded 1 in 60% yield. (Z)-4-Chloro-but-2-en-1-ol was prepared from cis-but-2-en-1-ol following the procedure of Colonge, J.; Poilane, G. Bull. Soc. Chim, Fr., 1955, 953-955.
    • (1955) Bull. Soc. Chim, Fr. , pp. 953-955
    • Colonge, J.1    Poilane, G.2
  • 29
    • 0025865630 scopus 로고
    • (b) For an excellent review on dianion chemistry see
    • (b) For an excellent review on dianion chemistry see: Thompson, C. M.; Green, D. L. C. Tetrahedron, 1991, 47, 4223-4285.
    • (1991) Tetrahedron , vol.47 , pp. 4223-4285
    • Thompson, C.M.1    Green, D.L.C.2
  • 31
    • 0345339993 scopus 로고    scopus 로고
    • note
    • Studies were not done to improve the selectivity. However, 2.2 equiv. of LDA instead of LiHMDS under similar conditions afforded 3a as a single diastereomer (95%) in 30% yield.
  • 32
    • 0344046175 scopus 로고    scopus 로고
    • note
    • +, calculated value=470.14598).
  • 37
    • 0344046172 scopus 로고    scopus 로고
    • note
    • 3N to obtain completely the cyclized compound after purification.
  • 38
    • 0344908836 scopus 로고    scopus 로고
    • note
    • +, calculated value=314.12148).
  • 39
    • 0345339989 scopus 로고    scopus 로고
    • NOE details
    • NOE details:
  • 40
    • 0345339988 scopus 로고    scopus 로고
    • note
    • 3P (1.4 equiv.) in THF under an argon atmosphere and after 15 min 4f (1 equiv. in THF) was added at -10°C. The mixture was slowly warmed to RT and then stirred for 12 h. The solvent was removed under reduced pressure and the residue was chromatographed in a silica gel flash column using EtOAc and then 5% MeOH in EtOAc.
  • 44
    • 85093693595 scopus 로고
    • (c) and 704
    • (c) Spath, E.; Kesztler, F. Ber., 1937, 70, 239 and 704.
    • (1937) Ber. , vol.70 , pp. 239
    • Spath, E.1    Kesztler, F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.