Fully elaborated carbon functionalized

The synthesis of a fully functionalized cyclopentane core structure of pactamycin, a potent antitumor antibiotic, involves Overman rearrangement as a key reaction. Heating a mixture of potassium carbonate and the imidate derived from allylic alcohol 68 in p-xylene yields the desired trichloroacetamide 69 as a single isomer in 90% yield from 68. In this reaction, potassium carbonate is a crucial additive as no desired product is obtained when the same reaction is carried out without potassium carbonate. Trichloroacetimidate 69 has been elaborated into the tricyclic compound 70 which contains all the carbon atoms for the core cyclopentane of pactamycin,... 

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