New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method
Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-arylβ-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of (3R,4S-N-benzoyl-3-(1-ethoxy-ethoxy)-4-phenyl-2-azetidinone which is coupled with protected baccatin IIIs, followed by deprotection to give optically pure taxol and 10-deacetyl-7,10-bis(Troc)-taxol in good yields.
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