Synthesis of docetaxel and butitaxel analogues through kinetic resolution of racemic β-lactams with 7-O-triethylsilylbaccatin III

Haibo Ge, Jared T. Spletstoser, Yan Yang, Margaret Kayser, Gunda I. Georg

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

(Chemical Equation Presented) The kinetic resolution of racemic cis-4-phenyl- and cis-4-tert-butyl-3-hydroxy-β-lactam derivatives with 7-O-triethylsilylbaccatin III yielded paclitaxel and butitaxel analogues with high diastereoselectivity. The results demonstrated that the tert-butyldimethylsilyl protecting group at the C3-hydroxy group of the β-lactams provided optimum kinetic resolution in comparison with the sterically less demanding triethylsilyl group and the larger triisopropylsilyl group. In addition, it was found that the C4 β-lactam substituents also influenced diastereoselectivity. The C4 tert-butyl-β-lactams provided better diastereoselectivity than the corresponding C4 phenyl β-lactams.

Original languageEnglish
Pages (from-to)756-759
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number3
DOIs
StatePublished - Feb 2 2007

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