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Enantioselective synthesis of a taxol C-ring fragment containing an allylsilane moiety is described. Diastereoselective [4 + 2] cycloaddition of the pyrone with (R)-t-butylbenzyl vinyl ether followed by appropriate transformations gave a mixture of two regioisomeric cyclohexenyl sulfides, which was converted to the title compound with almost complete diastereo- and enantioselectivities by treating...
Formal total synthesis of coriolin has been accomplished on the basis of a [3+2] cycloaddition reaction of a vinylsulfide with 3-(methylthio)-2-siloxyallyl cation. A five-membered vinylsulfide as a C ring unit was prepared in five steps from commercially available compounds. The first [3+2] cycloaddition reaction gave the BC ring intermediate, which was then converted into a bicyclic vinylsulfide...
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