Synthesis of oseltamivir and tamiphosphor from N-acetyl-D-glucosamine
1Department of Chemistry, National Taiwan University, Taipei 106, Taiwan. jmfang@ntu.edu.tw.
Organic & Biomolecular Chemistry
|October 11, 2013
Abstract:
Using N-acetyl-D-glucosamine as a starting material, the anti-influenza drugs oseltamivir and tamiphosphor were synthesized via a pivotal intermediate of aldehyde 8. An intramolecular Horner-Wadsworth-Emmons reaction was utilized to construct the highly functionalized cyclohexene ring. The existing N-acetyl group was transformed into an azido group for the subsequent aziridination, followed by implantation of a 3-pentoxy group of the desired stereochemistry.
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