Formal enantioselective syntheses of oseltamivir and tamiphosphor

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A new method for the synthesis of the influenza antiviral drugs oseltamivir and tamiphosphor starting from 4-hydroxycyclohexenone has been developed. Stereoselective aziridination of a protected 4-hydroxycyclohexenone was used as a key step and the aziridine formed was resolved enzymatically with a very high yield and enantiomeric excess. The subsequent conversion to oseltamivir and tamiphosphor diethyl ester in 10 or 12 additional steps and 22% or 19% yield from intermediate 7, respectively, is described.

Original languageEnglish
Pages (from-to)236-240
Number of pages5
JournalOrganic Chemistry Frontiers
Volume4
Issue number2
DOIs
Publication statusPublished - 1 Feb 2017

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Oseltamivir
Antiviral Agents
Esters
tamiphosphor
4-hydroxycyclohexenone
aziridine

Cite this

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abstract = "A new method for the synthesis of the influenza antiviral drugs oseltamivir and tamiphosphor starting from 4-hydroxycyclohexenone has been developed. Stereoselective aziridination of a protected 4-hydroxycyclohexenone was used as a key step and the aziridine formed was resolved enzymatically with a very high yield and enantiomeric excess. The subsequent conversion to oseltamivir and tamiphosphor diethyl ester in 10 or 12 additional steps and 22{\%} or 19{\%} yield from intermediate 7, respectively, is described.",
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Formal enantioselective syntheses of oseltamivir and tamiphosphor. / Silva, Saúl; Maycock, Christopher D.

In: Organic Chemistry Frontiers, Vol. 4, No. 2, 01.02.2017, p. 236-240.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Maycock, Christopher D.

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