Półsynteza taksolu- opracowanie

Półsynteza Taksolu
(z 10-deacetylobakatyny III)
The diagrams below show the semisynthesis of Taxol using the Potier and Greene method. The compounds being added in step 1 were large so that an even larger molecule could be added to the correct position in step 2. Due to the large size of the molecules, the process was lengthy and temperatures varied between 0 and 73 degrees Celsius producing a yield that was commercially viable. Step 1 The OH on ring C (figure) is protected with the triethylsilyl group
The OH on ring B is converted into acetic acid ester (with AcCl)
Step 2 (2R,3S)-N-benzoyl-O-(1-ethoxyethyl)-3-phenylisoserine was added to ring A
Step 3 The triethylsilyl group is removed
Part of the side arm (1-ethoxyetyl group) is removed to release OH group
Taksol
DMAP = 4-dimethylaminopyridine        DPC = di-2-pyridylcarbonate        Py = Pyridine        AcCl = Acetyl chloride              Et3Si = Triethylsilyl group        PhMe = Toluene ... zobacz całą notatkę