메뉴 건너뛰기




Volumn , Issue 7, 2005, Pages 1179-1181

Concise synthesis of the tricyclic skeleton of cylindricines using a radical cascade involving 6-endo selective cyclization

Author keywords

Acyl radical; Cyclizations; Cylindricine; Radical cascade; Regioselectivity

Indexed keywords

ACETYL CHLORIDE; ALCOHOL; ALKALOID DERIVATIVE; AMIDE; AMINE; AZO COMPOUND; AZOBIS(CYCLOHEXANECARBONITRILE); BROMIDE; BROMINE DERIVATIVE; CHLORIDE; CYANIDE; CYCLOHEXANE DERIVATIVE; CYCLOHEXANONE; CYLINDRICINE A; CYLINDRICINE B; CYLINDRICINE C; CYLINDRICINE D; CYLINDRICINE DERIVATIVE; CYLINDRICINE E; CYLINDRICINE F; CYLINDRICINE G; CYLINDRICINE H; CYLINDRICINE I; CYLINDRICINE J; CYLINDRICINE K; ENAMIDE; HYDROXYL GROUP; IMINE; LEPADIFORMINE; LITHIUM BROMIDE; PERHYDROPYRROLO[2,1 J]QUINOLINE DERIVATIVE; PYRROLE DERIVATIVE; QUINOLINE DERIVATIVE; TIN DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

EID: 18744402534     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-865236     Document Type: Conference Paper
Times cited : (20)

References (38)
  • 5
  • 23
    • 18744375019 scopus 로고    scopus 로고
    • note
    • 13C NMR spectrum, which showed the presence of a quaternary carbon atom (δ = 66.3 ppm).
  • 24
    • 4043118938 scopus 로고    scopus 로고
    • Reviews on the synthesis of five- and six-membered heterocyclic compounds using radical cyclizalion: (a) Majumdar, K. C.; Mukhopadhyay, P. P.; Basu, P. K. Heterocycles 2004, 63, 1903.
    • (2004) Heterocycles , vol.63 , pp. 1903
    • Majumdar, K.C.1    Mukhopadhyay, P.P.2    Basu, P.K.3
  • 25
    • 18744384487 scopus 로고    scopus 로고
    • Pelletire S.W., Ed.; Wiley: New York, Chap 4
    • (b) Li, J. J. Alkaloids: Chemical Perspectives, Vol. 5; Pelletire, S. W., Ed.; Wiley: New York, 2001, Chap. 4.
    • (2001) Alkaloids Chemical Perspectives , vol.5
    • Li, J.J.1
  • 26
    • 18744386508 scopus 로고    scopus 로고
    • note
    • 3.
  • 27
    • 18744375859 scopus 로고    scopus 로고
    • note
    • -1 due to the five-membered lactam.
  • 28
    • 0001312951 scopus 로고
    • Radical reactions of some sterically fixed 3-bromo-N-(cyclohex-1-enyl) propionamides, which are closely related to compound 8, leading to the formation of 6-endo cyclization product or a mixture of 6-endo and 5-exo cyclization products have been reported. See: Schultz, A. G.; Guzzo, P. R.; Nowak, D. M. J. Org. Chem. 1995, 60, 8044.
    • (1995) J. Org. Chem. , vol.60 , pp. 8044
    • Schultz, A.G.1    Guzzo, P.R.2    Nowak, D.M.3
  • 32
    • 18744398253 scopus 로고    scopus 로고
    • note
    • Crystallographic data of 13 and 21 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 262989 (13) and 262990 (21), respectively. Copies of these data may be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing data_request@ccdc. cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033.
  • 37
    • 18744395612 scopus 로고    scopus 로고
    • note
    • The structure of compound 20 was confirmed by transforming it to compound 8 by removal of the carbonyl group of the ketone.
  • 38
    • 18744372854 scopus 로고    scopus 로고
    • note
    • 2: C, 69.54; H, 8.27; N, 6.76. Found: C, 69.31; H, 8.42; N, 6.61.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.