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Volumn 1, Issue 17, 2003, Pages 3002-3003

Tautomeric selectivity towards colchicinoids in the tosylation of colchiceine on a heterogeneous, easily removable catalyst

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; CATALYST SELECTIVITY; CONDENSATION REACTIONS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR STRUCTURE; PHENOLS; REACTION KINETICS;

EID: 0141629772     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b307650b     Document Type: Article
Times cited : (3)

References (23)
  • 11
    • 77957769724 scopus 로고
    • Tropolonic colchicum alkaloids and allo congeners
    • (a) O. Boye and A. Brossi, Tropolonic colchicum alkaloids and allo congeners, Alkaloids (Academic Press), 1992, 41, 125
    • (1992) Alkaloids (Academic Press) , vol.41 , pp. 125
    • Boye, O.1    Brossi, A.2
  • 13
    • 84980245367 scopus 로고    scopus 로고
    • note
    • The last step of several classical colchicine total syntheses (see, for example, J. Schreiber, W. Leimgruber, M. Pesaro, P. Schudel, T. Threlfall and A. Eschenmoser, Helv. Chim. Acta, 1961, 44, 540; J. Martel, E. Toromanoff and C. Huynh, J. Org. Chem., 1965, 30, 1752; D. L. Boger and C. E. Brotherton, J. Am. chem. Soc., 1986, 108, 6713) consists of alkylation of colchiceine, which, in current methodologies, such as diazomethane treatment (M. Sorkin, Helv. Chim. Acta, 1946, 29, 246) suffers from preferential isocolchicine formation (55 : 45). The Amberlite route provided here may considerably enhance the yield of the process.
  • 16
    • 0141551179 scopus 로고
    • (b) J. C. Gage, Analyst, 1957, 82, 219
    • (1957) Analyst , vol.82 , pp. 219
    • Gage, J.C.1
  • 21
    • 0141439676 scopus 로고    scopus 로고
    • note
    • a for brucine and DABCO are too close together for the observed yield inversion (Table 1) to be significant.
  • 22
    • 0141662575 scopus 로고    scopus 로고
    • note
    • a values 7.70 and 7.24 for 1a and 1b, respectively.
  • 23
    • 0013159053 scopus 로고
    • note
    • Nucleophilic substitutions on colchicides and isocolchicides bearing an α-leaving group were previously compared: M. Cavazza and F. Pietra, J. Chem. Soc., Perkin Trans. 1, 1995, 2657.
    • (1995) J. Chem. Soc., Perkin Trans. 1 , pp. 2657
    • Cavazza, M.1    Pietra, F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.