Development of a Concise Synthesis of (−)‐Oseltamivir (Tamiflu) | Zendy

Trost Barry M. | Zendy; Zhang Ting | Zendy

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Development of a Concise Synthesis of (−)‐Oseltamivir (Tamiflu)

Author(s) -

Trost Barry M.,

Zhang Ting

Publication year - 2011

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201003454

Subject(s) - stereoselectivity , oseltamivir , yield (engineering) , combinatorial chemistry , tsuji–trost reaction , alkylation , palladium , chemistry , rhodium , catalysis , enantioselective synthesis , organic chemistry , materials science , covid-19 , medicine , disease , pathology , infectious disease (medical specialty) , metallurgy

We report a full account of our work towards the development of an eight‐step synthesis of anti‐influenza drug (−)‐oseltamivir (Tamiflu) from commercially available starting materials. The final synthetic route proceeds with an overall yield of 30 %. Key transformations include a novel palladium‐catalyzed asymmetric allylic alkylation reaction (Pd‐AAA) as well as a rhodium‐catalyzed chemo‐, regio‐, and stereoselective aziridination reaction.

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