N-methylation of the C3′ amide of taxanes: Synthesis of N-methyltaxol C and N-methylpaclitaxel

Hari K.R. Santhapuram, Apurba Datta, Oliver E. Hutt, Gunda I. Georg

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)4705-4708
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number12
DOIs
StatePublished - Jun 20 2008

Fingerprint

Dive into the research topics of 'N-methylation of the C3′ amide of taxanes: Synthesis of N-methyltaxol C and N-methylpaclitaxel'. Together they form a unique fingerprint.

Cite this