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Synlett 2020; 31(19): 1925-1929
DOI: 10.1055/s-0039-1690878
DOI: 10.1055/s-0039-1690878
cluster
Continuous-Flow Synthesis of (–)-Oseltamivir Phosphate (Tamiflu)
We thank the National Research Foundation (NRF SARChI Grant), Council for Scientific and Industrial Research (CSIR-DST Grant) and Nelson Mandela University for financial support.Further Information
Publication History
Received: 27 February 2020
Accepted after revision: 13 March 2020
Publication Date:
24 April 2020 (online)
Published as part of the Cluster Integrated Synthesis Using Continuous-Flow Technologies
Abstract
Herein the anti-influenza drug (–)-oseltamivir phosphate is prepared in continuous flow from ethyl shikimate with 54% overall yield over nine steps and total residence time of 3.5 min from the individual steps. Although the procedure involved intermediate isolation, the dangerous azide chemistry and intermediates involved were elegantly handled in situ. It is the first continuous-flow process for (–)-oseltamivir phosphate involving azide chemistry and (–)-shikimic acid as precursor.
Key words
azide chemistry - continuous flow - influenza - (–)-oseltamivir phosphate - total synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690878.
- Supporting Information
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