Tatsuya Nitabaru, Dr. Naoya Kumagai and Prof. Dr. Masakatsu Shibasaki Catalytic Asymmetric anti-Selective Nitroaldol Reaction En Route to Zanamivir Angewandte Chemie International Edition 51
Battling the flu: Zanamivir (Relenza) is widely prescribed as an anti-influenza drug. It contains a vicinal amino alcohol, which is in an anti orientation, and is readily accessed by an anti-selective catalytic asymmetric nitroaldol (Henry) reaction promoted by a heterobimetallic complex (see scheme; PMB=p-methoxybenzyl). Additional synthetic manipulation of the nitroaldol product allowed the enantioselective synthesis of zanamivir.
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