N-methylation of the c3' amide of taxanes: synthesis of N-methyltaxol C and N-methylpaclitaxel.
A method has been developed for the methylation of the C3' amide of taxol C and paclitaxel. Taxol C and paclitaxel were sequentially silylated at the 2', 7, and 1-hydroxyl groups with tert-butyldimethylsilyl chloride, triethylsilyl chloride, and dimethylsilyl chloride, respectively. Subsequent reaction with potassium tert-butoxide and methyl iodide provided the corresponding N-methylated taxane derivatives. Removal of the silyl protecting groups furnished N-methyltaxol C and N-methylpaclitaxel.
Santhapuram
Hari K R
HK
Department of Medicinal Chemistry, University of Kansas, Lawrence, KS 66045-7582, USA.
Datta
Apurba
A
Hutt
Oliver E
OE
Georg
Gunda I
GI
D000577:Amides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D043823:Taxoids / Q000138:chemical synthesis / Q000737:chemistry*
D000577:Amides; D043823:Taxoids