ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
N-Deacetylcolchiceine (7), readily available from colchicine (1), was converted into N-trifluoroacetyl-deacetylcolchiceine (8). Methylation of 8 with methyl iodide in the presence of potassium carbonate afforded a mixture of N-trifluoroacetyl-demecolcine (10) and its isomer 11. The mixture of 10 and 11 was detrifluoroacetylated and separated by chromatography to afford demecolcine (2) and isodemecolcine (12). A more practical route to 2 started with 8, and gave N-trifluoroacetyl-deacetylcolchicine (13) and its isomer 14 after O-methylation with diazomethane. N-Methylation of 13 and 14 with methyl iodide and potassium carbonate afforded 10 and 11. The overall yield in the conversion of colchicine (1) into demecolcine (2) via 7, 8 and 13 was 55%.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19790620406
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