The Path To Synthesis

Step 10 &mdash deprotection of 2´,7-bis(triethylsilyl) taxol

      A negative fluoride ion, from HF, will remove the triethylsilyl group from the oxygen that was protected previously. The SN2 reaction will leave an extra electron on the oxygen, which will then capture a hydrogen ion to reform the hydroxyl group.

      This same reaction is repeated for the protected alcohol at carbon #2´ of the side chain.

      Once both alcohols have been de-protected, the synthesis of taxol is completed.

Credits &rArr          

© 2009 Matthew Radcliff and Dr. Joseph Fox
Created with funding provided by
the Camille & Henry Dreyfus Foundation Special Grant Program in the Chemical Sciences
and the National Science Foundation