메뉴 건너뛰기




Volumn 124, Issue 50, 2002, Pages 14826-14827

First total synthesis of (±)-strychnofoline via a highly selective ring-expansion reaction

Author keywords

[No Author keywords available]

Indexed keywords

PLANT EXTRACT; STRYCHNOFOLINE; UNCLASSIFIED DRUG;

EID: 0037132663     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027906k     Document Type: Article
Times cited : (156)

References (23)
  • 16
    • 0000794592 scopus 로고    scopus 로고
    • The facile conversion of the lactamol into the enamine was surprising, considering that other less substituted lactamols were converted into the corresponding enamine only upon heating to 160 °C in HMPA for several hours: Dieter, R. K.; Sharma, R. R. J. Org. Chem. 1996, 61, 4180-4184.
    • (1996) J. Org. Chem. , vol.61 , pp. 4180-4184
    • Dieter, R.K.1    Sharma, R.R.2
  • 17
    • 0012190166 scopus 로고    scopus 로고
    • note
    • The synthesis of 17 commences with 6-methoxyisatine which is commercially available, see Supporting Information.
  • 18
    • 0012108219 scopus 로고    scopus 로고
    • note
    • β at C-14.
  • 19
    • 0012108528 scopus 로고
    • Saxon, J. E., Ed.; Wiley-Interscience: New York
    • For an in-depth discussion, see: Brown, R. T. In Heterocyclic Compounds; Saxon, J. E., Ed.; Wiley-Interscience: New York, 1983; Vol. 25, Part 4, pp 85-97.
    • (1983) Heterocyclic Compounds , vol.25 , Issue.PART 4 , pp. 85-97
    • Brown, R.T.1
  • 20
    • 0012108220 scopus 로고    scopus 로고
    • note
    • 1H NMR, see Supporting Information.
  • 22
    • 0012187623 scopus 로고    scopus 로고
    • Although we did not anticipate stereoselectivity in this condensation reaction of the simple tryptamine derivative, it is important to note that stereoselective Pictet Spengler reactions have been documented employing tryptophan derivatives. Application of such methods at this stage would likely provide the desired product stereoselectively. Watson, W. H.; Krawiec, M. J.; Cox, E. D.; Hamaker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennet, D. W.; Cook, J. M. J. Org. Chem. 1997, 62, 44-61.
    • (1997) J. Org. Chem. , vol.62 , pp. 44-61
    • Watson, W.H.1    Krawiec, M.J.2    Cox, E.D.3    Hamaker, L.K.4    Li, J.5    Yu, P.6    Czerwinski, K.M.7    Deng, L.8    Bennet, D.W.9    Cook, J.M.10


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.