Convergence with Mutual Kinetic Resolution. 1. Studies Defining Methodology for the Taxol C/D Ring Fragment and Synthezis of the A Ring Fragment

Article abstract of DOI:10.1021/jo00226a005

4-Exo-tet cyclization gives the alkoxyoxethane of the taxol C/D ring fragment if the tertiary alcohol is protected.Cycloaddition of dichloroketene and 1-<(tert-butyldimethylsilyl)oxy>-2-methylcyclohex-2-ene, a model for the allylic ether 6, succeeds in the presence of DME.The synthesis of the A ring fragment relies on the Diels-Alder reaction of 1-ethoxy-3-<(trimethylsilyl)oxy>-2-methyl-1,3-butadiene with ethyl (E)-2-acetoxyacrylate and the axial conjugate addition of a vinyl Normant reagent.