Catalytic asymmetric anti-selective nitroaldol reaction en Route to Zanamivir

Tatsuya Nitabaru, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

52 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 languageEnglish
Pages (from-to)1644-1647
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number7
DOIs
Publication statusPublished - 2012 Feb 13
Externally publishedYes

Keywords

  • heterometallic complexes
  • inhibitors
  • nitroaldol reaction
  • synthetic methods
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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