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Development of a concise synthesis of (-)-oseltamivir (Tamiflu).

ABSTRACT: 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.

SUBMITTER: Trost BM

PROVIDER: S-EPMC3079541 | biostudies-literature | 2011 Mar

REPOSITORIES: biostudies-literature

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Development of a concise synthesis of (-)-oseltamivir (Tamiflu).

Trost Barry M BM Zhang Ting T

Chemistry (Weinheim an der Bergstrasse, Germany) 20110301 13

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. ...[more]

PMID: 21365707

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