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Catalytic Asymmetric anti-Selective Nitroaldol Reaction En Route to Zanamivir

Authors


  • This work was financially supported by KAKENHI (No. 20229001 and 23590038) from the JSPS. Dr. Sandeep Chaudhary was gratefully acknowledged for the synthesis of key substrates. We thank Dr. Ryuichi Sawa and Ms. Yumiko Kubota for detailed NMR and HRMS analyses. N.K. thanks the Uehara Memorial Foundation for financial support. T.N. thanks JSPS for predoctoral fellowship.

Abstract

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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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