Jump to main content
Jump to site search

Issue 20, 2012
Previous Article Next Article

Synthesis of the anti-influenza agent (−)-oseltamivir free base and (−)-methyl 3-epi-shikimate

Author affiliations

Abstract

A new enantioselective synthesis of the anti-influenza agent (−)-oseltamivir free base (7.1% overall yield; 98% ee) and (−)-methyl 3-epi-shikimate (16% overall yield; 98% ee) has been described from readily available raw materials. Sharpless asymmetric epoxidation and diastereoselective Barbier allylation of an aldehyde are the key reactions employed in the incorporation of chirality, while the cyclohexene carboxylic ester core was constructed through a ring closing metathesis reaction.

Graphical abstract: Synthesis of the anti-influenza agent (−)-oseltamivir free base and (−)-methyl 3-epi-shikimate

Back to tab navigation

Supplementary files

Publication details

The article was received on 28 Mar 2012, accepted on 11 Apr 2012 and first published on 13 Apr 2012


Article type: Communication
DOI: 10.1039/C2OB25635E
Citation: Org. Biomol. Chem., 2012,10, 3988-3990
  •   Request permissions

    Synthesis of the anti-influenza agent (−)-oseltamivir free base and (−)-methyl 3-epi-shikimate

    V. Rawat, S. Dey and A. Sudalai, Org. Biomol. Chem., 2012, 10, 3988
    DOI: 10.1039/C2OB25635E

Search articles by author

Spotlight

Advertisements