메뉴 건너뛰기




Volumn 50, Issue 20, 2009, Pages 2411-2413

A novel and efficient total synthesis of (±)-physostigmine

Author keywords

[No Author keywords available]

Indexed keywords

PHYSOSTIGMINE;

EID: 63349092149     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.012     Document Type: Article
Times cited : (28)

References (127)
  • 3
    • 0043288716 scopus 로고
    • For a review, see:
    • For a review, see:. Hino T., and Nakagawa M. Alkaloids 34 (1989) 1-75
    • (1989) Alkaloids , vol.34 , pp. 1-75
    • Hino, T.1    Nakagawa, M.2
  • 14
    • 16844383145 scopus 로고    scopus 로고
    • For 3a-substituted pyrrolidinoindolines (other than physostigmine), see:
    • For 3a-substituted pyrrolidinoindolines (other than physostigmine), see:. Kimura M., Futamata M., Mukai R., and Tamaru Y. J. Am. Chem. Soc. 127 (2005) 4592
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 4592
    • Kimura, M.1    Futamata, M.2    Mukai, R.3    Tamaru, Y.4
  • 51
    • 0001683943 scopus 로고
    • For racemic synthesis of physostigmine, see:
    • For racemic synthesis of physostigmine, see:. Julian P.L., and Pikl J. J. Am. Chem. Soc. 57 (1935) 563-566
    • (1935) J. Am. Chem. Soc. , vol.57 , pp. 563-566
    • Julian, P.L.1    Pikl, J.2
  • 84
    • 0032496928 scopus 로고    scopus 로고
    • For chiral synthesis of physostigmine, see:
    • For chiral synthesis of physostigmine, see:. Matsuura T., Overman L.E., and Poon D.J. J. Am. Chem. Soc. 120 (1998) 6500-6503
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6500-6503
    • Matsuura, T.1    Overman, L.E.2    Poon, D.J.3
  • 123
    • 63349101577 scopus 로고    scopus 로고
    • note
    • The olefinic proton appearing as a singlet at δ 6.10 ppm is due the E-isomer, while the singlet at 6.04 ppm is due the Z-isomer. Similarly, the methyl signal at 1.92 ppm is due the E-isomer and signal at 1.95 ppm is due the Z-isomer. The ratio of E-methyl to Z-methyl is 5:1, the same ratio is observed for the olefinic E-H to Z-H. Further the terminal and internal protons of the monosubstituted olefin and the allylic protons show two sets of the signals in ratio of 5:1. This confirmed that the compound in hand is the mixture of the 5:1 ratio of E-and Z-isomer obtained from the Wittig reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.