Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 42, Pages 12616-12626Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201001108
Keywords
asymmetric synthesis; domino reactions; organocatalysis; Tamiflu
Categories
Funding
- Nagase Science and Technology Foundation, Japan
Ask authors/readers for more resources
The efficient asymmetric total synthesis of (-)-oseltamivir, an antiviral reagent, has been accomplished by using two one-pot reaction sequences, with excellent overall yield (60%) and only one required purification by column chromatography. The first one-pot reaction sequence consists of a diphenylprolinol silyl ether mediated asymmetric Michael reaction, a domino Michael reaction/Horner-Wadsworth-Emmons reaction combined with retro-aldol/Horner-Wadsworth-Emmons reaction and retro Michael reactions, a thiol Michael reaction, and a base-catalyzed isomerization. Six reactions can be successfully conducted in the second one-pot reaction sequence; these are deprotection of a tert-butyl ester and its conversion into an acyl chloride then an acyl azide, Curtius rearrangement, amide formation, reduction of a nitro group into an amine, and a retro Michael reaction of a thiol moiety. A column-free synthesis of (-)-oseltamivir has also been established.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available