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Volumn 48, Issue 34, 2007, Pages 5942-5947

An enantiospecific synthesis of (+)-demethoxyerythratidinone from (S)-malic acid: key observations concerning the diastereocontrol in malic acid-derived N-acyliminium ion cyclisations

Author keywords

3 Demethoxyerythratidinone; Alkaloid; Cyclisation; N Acyliminium; Total synthesis

Indexed keywords

3 DEMETHOXYERYTHRATIDINONE; ALCOHOL; DEMETHOXYERYTHRATIDINONE; IMINE; LACTAM DERIVATIVE; MALIC ACID DERIVATIVE; N ACYLIMINIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34447628833     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.111     Document Type: Article
Times cited : (33)

References (28)
  • 13
    • 2942648353 scopus 로고    scopus 로고
    • For an overview of pioneering work towards erythrinan alkaloids using N-acyliminium chemistry see Ref.1d. Asymmetric synthesis:
    • For an overview of pioneering work towards erythrinan alkaloids using N-acyliminium chemistry see Ref.1d. Asymmetric synthesis:. Allin S.M., Streetley G.B., Slater M., James S.L., and Martin W.P. Tetrahedron Lett. 45 (2004) 5493
    • (2004) Tetrahedron Lett. , vol.45 , pp. 5493
    • Allin, S.M.1    Streetley, G.B.2    Slater, M.3    James, S.L.4    Martin, W.P.5
  • 17
    • 34447649787 scopus 로고    scopus 로고
    • note
    • The ee was determined as 47% by HPLC (Chiracel OD Column, 20% IPA in hexane, 0.4 mL/min); the retention times were 23.4 min (minor) and 31.2 min (major).
  • 19
    • 33846107960 scopus 로고    scopus 로고
    • For a relevant computational study, see:
    • For a relevant computational study, see:. Ye J.-L., Huang P.-Q., and Lu X. J. Org. Chem. 72 (2007) 35
    • (2007) J. Org. Chem. , vol.72 , pp. 35
    • Ye, J.-L.1    Huang, P.-Q.2    Lu, X.3
  • 20
    • 34447625779 scopus 로고    scopus 로고
    • note
    • The crystal structure has been deposited at the Cambridge Crystallographic Data Centre; Deposition Number CCDC 646549.
  • 26
    • 0037145003 scopus 로고    scopus 로고
    • Pilli has proposed a somewhat similar explanation for reactions of related regioisomeric lactams, see:
    • Pilli has proposed a somewhat similar explanation for reactions of related regioisomeric lactams, see:. Schuch C.M., and Pilli R.A. Tetrahedron: Asymmetry 13 (2002) 1973
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 1973
    • Schuch, C.M.1    Pilli, R.A.2
  • 27
    • 34447641694 scopus 로고    scopus 로고
    • note
    • ++Na): 3...
  • 28
    • 34447632077 scopus 로고    scopus 로고
    • note
    • Despite the natural product having been prepared a number of times there are scant data readily available in the literature because so many reports concern formal syntheses that converge on late Tsuda intermediates, see Ref. 6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.