Catalytic asymmetric anti-selective nitroaldol reaction en Route to Zanamivir

Tatsuya Nitabaru; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1002/anie.201108153

Catalytic asymmetric anti-selective nitroaldol reaction en Route to Zanamivir

Tatsuya Nitabaru, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journal › Article › peer-review

53 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1644-1647
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	7
DOIs	https://doi.org/10.1002/anie.201108153
Publication status	Published - 2012 Feb 13
Externally published	Yes

Keywords

heterometallic complexes
inhibitors
nitroaldol reaction
synthetic methods
total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201108153

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AU - Shibasaki, Masakatsu

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Y1 - 2012/2/13

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AB - 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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KW - inhibitors

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KW - synthetic methods

KW - total synthesis

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Catalytic asymmetric anti-selective nitroaldol reaction en Route to Zanamivir

Abstract

Keywords

ASJC Scopus subject areas

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