Literature DB >> 19366236

A short and practical synthesis of oseltamivir phosphate (Tamiflu) from (-)-shikimic acid.

Liang-Deng Nie1, Xiao-Xin Shi, Kwang Hyok Ko, Wei-Dong Lu.   

Abstract

Oseltamivir phosphate (1) was synthesized from (-)-shikimic acid through a short and practical synthetic route via eight steps in 47% overall yield. In addition, the highly regioselective and stereoselective nucleophilic replacement of OMs by the N(3) group in the third and seventh steps has been studied in detail, and the reaction conditions were optimized.

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Year:  2009        PMID： 19366236     DOI： 10.1021/jo900218k

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


  10 in total

1.  Glycomimetic building blocks: a divergent synthesis of epimers of shikimic acid.

Authors:  Joseph C Grim; Kathleen C A Garber; Laura L Kiessling
Journal:  Org Lett       Date:  2011-06-28       Impact factor: 6.005

2.  Novel stereoselective syntheses of N-octyl-β-valienamine (NOV) and N-octyl-4-epi-β-valienamine (NOEV) from (-)-shikimic acid.

Authors:  Feng-Lei Li; Jiang-Ping Yu; Wei Ding; Mian-Mian Sun; Yun-Gang He; Xing-Liang Zhu; Shi-Ling Liu; Xiao-Xin Shi
Journal:  RSC Adv       Date:  2019-12-18       Impact factor: 4.036

3.  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

4.  Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines.

Authors:  Melinda Nonn; Loránd Kiss; Reijo Sillanpää; Ferenc Fülöp
Journal:  Beilstein J Org Chem       Date:  2012-01-17       Impact factor: 2.883

5.  Global ecological regionalization of 15 Illicium species: nature sources of shikimic acid.

Authors:  Xiang Zhang; Xiangxiao Meng; Jie Wu; Linfang Huang; Shilin Chen
Journal:  Chin Med       Date:  2018-06-15       Impact factor: 5.455

6.  Efficient and Highly Stereoselective Syntheses of (+)-proto-Quercitol and (-)-gala-Quercitol Starting from the Naturally Abundant (-)-Shikimic Acid.

Authors:  Xing-Liang Zhu; Lei Wang; Yong-Qiang Luo; Yun-Gang He; Feng-Lei Li; Mian-Mian Sun; Shi-Ling Liu; Xiao-Xin Shi
Journal:  ACS Omega       Date:  2020-01-21

7.  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

Review 8.  Recent progress in chemical approaches for the development of novel neuraminidase inhibitors.

Authors:  Ahmed Mahal; Meitao Duan; Dhafer S Zinad; Ranjan K Mohapatra; Ahmad J Obaidullah; Xiaoyi Wei; Manoj K Pradhan; Debadutta Das; Venkataramana Kandi; Hany S Zinad; Quanhong Zhu
Journal:  RSC Adv       Date:  2021-01-06       Impact factor: 3.361

9.  Novel Stereoselective Syntheses of (+)-Streptol and (-)-1-epi-Streptol Starting from Naturally Abundant (-)-Shikimic Acid.

Authors:  Xing-Liang Zhu; Yong-Qiang Luo; Lei Wang; Yong-Kang Huang; Yun-Gang He; Wen-Jing Xie; Shi-Ling Liu; Xiao-Xin Shi
Journal:  ACS Omega       Date:  2021-06-23

Review 10.  The evolution of Tamiflu synthesis, 20 years on: Advent of enabling technologies the last piece of the puzzle?

Authors:  Cloudius R Sagandira; Francis M Mathe; Upenyu Guyo; Paul Watts
Journal:  Tetrahedron       Date:  2020-07-26       Impact factor: 2.457
  10 in total

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