Total Synthesis of the Cytotoxic Enehydrazide Natural Products Hydrazidomycins A and B by a Carbazate Addition/Peterson Olefination Approach
2013
Beveridge, Ramsay E. | Batey, Robert A.
The first total syntheses of two natural antitumor enehydrazide compounds (hydrazidomycins A and B) and a related positional isomer of hydrazidomycin B (elaiomycin B) have been accomplished in a rapid and stereocontrolled fashion using a Peterson elimination approach. A regioselective silyl epoxide ring opening reaction with Boc-carbazate followed by base-mediated Peterson siloxide elimination stereospecifically installed the key Z-enehydrazide functionality. The use of Boc-carbazate allowed for the differential functionalization of the hydrazide nitrogens.
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