Synthesis of the anti-influenza agent (-)-oseltamivir free base and (-)-methyl 3-epi-shikimate |
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Authors: | Rawat Varun Dey Soumen Sudalai Arumugam |
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Affiliation: | Chemical Engineering and Process Development Division, National Chemical Laboratoty, Pashan Road, Pune 411008, India. |
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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. |
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