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Volumn 8, Issue 7, 2006, Pages 1295-1297

Formal total synthesis of (-)-emetine using catalytic asymmetric allylation of cyclic imines as a key step

Author keywords

[No Author keywords available]

Indexed keywords

EMETINE; IMINE;

EID: 33645957099     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0530326     Document Type: Article
Times cited : (100)

References (36)
  • 18
    • 0029812556 scopus 로고    scopus 로고
    • and references therein
    • There are a few reports which claimed the asymmetric allylation using a stoichiometrical amount of chiral compound; see: Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996. 118, 8489 and references therein.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8489
    • Nakamura, M.1    Hirai, A.2    Nakamura, E.3
  • 20
    • 33645933360 scopus 로고    scopus 로고
    • note
    • With three times of careful recrystallization, the tartrate salt of racemic 2 afforded the enantiomeric 2 in 97% ee.
  • 21
    • 33645923485 scopus 로고    scopus 로고
    • note
    • The absolute configuration of the compound 2 was determined by the transformation to the known compound 10.
  • 24
    • 33645914515 scopus 로고    scopus 로고
    • note
    • Other than the reported method that used ethanedithiol-TFA followed by Raney Ni, several reduction systems were tested which involve various variants of Wolff-Kishner or Clemmensen reduction, but the product 7 was not obtained in more than 7% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.