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Angew Chem Int Ed Engl. 2012 Jan 10. doi: 10.1002/anie.201108153. [Epub ahead of print]
Catalytic Asymmetric anti-Selective Nitroaldol Reaction En Route to Zanamivir.
Nitabaru T, Kumagai N, Shibasaki M.
Source
Institute of Microbial Chemistry, Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan) http://www.bikaken.or.jp/research/gr.../index_e.html; Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033 (Japan).
Abstract
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.
Copyright ? 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PMID:
22234923
[PubMed - as supplied by publisher]
Catalytic Asymmetric anti-Selective Nitroaldol Reaction En Route to Zanamivir.
Nitabaru T, Kumagai N, Shibasaki M.
Source
Institute of Microbial Chemistry, Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan) http://www.bikaken.or.jp/research/gr.../index_e.html; Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033 (Japan).
Abstract
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.
Copyright ? 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PMID:
22234923
[PubMed - as supplied by publisher]
