Direct, stereoselective synthesis of the protected paclitaxel (taxol) side chain and high-yield transformation to paclitaxel
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 22,p. 2591-2592
- https://doi.org/10.1039/c39940002591
Abstract
A short, efficient approach to the p-methoxybenzylidene-protected paclitaxel (Taxol) side chain through benzaldehyde benzoylimine-chiral enolate condensation, followed by DDQ-mediated oxazolidine formation and hydrolysis is described; the C-7-triethylsilyl derivative of baccatin III undergoes esterification with this side chain in the presence of DCC and DMAP to provide after acid hydrolysis paclitaxel in excellent overall yield.Keywords
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