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Merck

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

Organic & biomolecular chemistry (2012-04-24)
Varun Rawat, Soumen Dey, Arumugam Sudalai
ZUSAMMENFASSUNG

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.

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Sigma-Aldrich
Shikimisäure, ≥99%
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Supelco
Shikimisäure, analytical standard
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