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Volumn 67, Issue 38, 2011, Pages 7412-7417

Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide

Author keywords

Epiquinamide; Intramolecular aza Michael reaction; Lupinine; Myrtine; Organocatalysis; Quinolizidine alkaloids

Indexed keywords

EPIEPIQUINAMIDE; LUPININE; MYRTINE; QUINOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 80051795519     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.07.017     Document Type: Article
Times cited : (38)

References (58)
  • 5
    • 80051780686 scopus 로고    scopus 로고
    • For recent reviews on organocatalysis, see
    • For recent reviews on organocatalysis, see
  • 10
    • 80051791458 scopus 로고    scopus 로고
    • For recent reviews on asymmetric enantioselective aza-Michael reactions, see
    • For recent reviews on asymmetric enantioselective aza-Michael reactions, see
  • 29
    • 80051784847 scopus 로고    scopus 로고
    • 3-CHCH-MgBr to aldehyde 5 and subsequent oxidation. However, following this sequence, conjugated ketone 8 was obtained in lower yield (when compared to the three step procedure showed in Scheme 3) and as a 2:1 mixture of cis and trans diastereoisomers.
    • 3-CHCH-MgBr to aldehyde 5 and subsequent oxidation. However, following this sequence, conjugated ketone 8 was obtained in lower yield (when compared to the three step procedure showed in Scheme 3) and as a 2:1 mixture of cis and trans diastereoisomers.
  • 30
    • 80051802688 scopus 로고    scopus 로고
    • 3, TBAF or t-BuOK, although with some erosion of the final yield.
    • 3, TBAF or t-BuOK, although with some erosion of the final yield.
  • 42
    • 80051801875 scopus 로고    scopus 로고
    • Ref. 12a,b.
    • Ref. 12a,b.
  • 53
    • 80051789400 scopus 로고    scopus 로고
    • The diastereoselectivity of the allylation reaction was determined by GC-MS. Compound 10 was previously described by using a different allylation methodology (see Ref. 13f) although with poor selectivity.
    • The diastereoselectivity of the allylation reaction was determined by GC-MS. Compound 10 was previously described by using a different allylation methodology (see Ref. 13f) although with poor selectivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.