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Simple Conversion of Colchicine into Demecolcine
Author(s) -
Capraro HansGeorg,
Brossi Arnold
Publication year - 1979
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19790620406
Subject(s) - chemistry , colchicine , diazomethane , potassium carbonate , yield (engineering) , methyl iodide , potassium , methylation , organic chemistry , biochemistry , medicine , materials science , metallurgy , gene
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%.