Total Synthesis of (±)-Halomon by a Johnson-Claisen Rearrangement.
Schlama T., Baati R., Gouverneur V., Valleix A., Falck JR., Mioskowski C.
The total synthesis of the polyhalogenated antitumour agent halomon (1) was accomplished with two novel transformations as key steps: a Johnson-Claisen rearrangement of a dichlorinated alkene for the preparation of the tertiary chlorinated C3 and a new rearrangement of bromohydrins for the regiospecific introduction of the bromine and chlorine atoms on C6 and C7, respectively.