Literature DB >> 20394411

A practical and azide-free synthetic approach to oseltamivir from diethyl D-tartrate.

Jiang Weng1, Yong-Bo Li, Rui-Bin Wang, Feng-Quan Li, Can Liu, Albert S C Chan, Gui Lu.   

Abstract

A short and practical synthesis of oseltamivir was accomplished in 11 steps from inexpensive and abundant diethyl D-tartrate starting material. This azide-free route featured an asymmetric aza-Henry reaction and a domino nitro-Michael/Horner-Wadsworth-Emmons (HWE) reaction as the key steps to construct the relevant cyclohexene ring of the product, which provided an economical and practical alternative for the synthesis of oseltamivir.

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Year:  2010        PMID： 20394411     DOI： 10.1021/jo100187m

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  Enantioselective Synthesis of Oseltamivir Phosphate (Tamiflu) via the Iron-Catalyzed Stereoselective Olefin Diazidation.

Authors:  Hongze Li; Shou-Jie Shen; Cheng-Liang Zhu; Hao Xu
Journal:  J Am Chem Soc       Date:  2018-08-09       Impact factor: 15.419

2.  Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology.

Authors:  Cloudius R Sagandira; Paul Watts
Journal:  Beilstein J Org Chem       Date:  2019-10-30       Impact factor: 2.883

3.  Synthesis of the reported structure of piperazirum using a nitro-Mannich reaction as the key stereochemical determining step.

Authors:  James C Anderson; Andreas S Kalogirou; Michael J Porter; Graham J Tizzard
Journal:  Beilstein J Org Chem       Date:  2013-08-23       Impact factor: 2.883

4.  One-pot multicomponent nitro-Mannich reaction using a heterogeneous catalyst under solvent-free conditions.

Authors:  Giovanna Bosica; Ramon Zammit
Journal:  PeerJ       Date:  2018-06-27       Impact factor: 2.984
  4 in total

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