A novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (−)-shikimic acid

2009 ◽  
Vol 20 (1) ◽  
pp. 124-129 ◽  
Author(s):  
Liang-Deng Nie ◽  
Xiao-Xin Shi
Keyword(s):  
Asymmetric Synthesis ◽  
Shikimic Acid ◽  
Oseltamivir Phosphate

Novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (−)-shikimic acid via cyclic sulfite intermediates

2011 ◽  
Vol 22 (16-17) ◽  
pp. 1692-1699 ◽  
Author(s):  
Liang-Deng Nie ◽  
Xiao-Xin Shi ◽  
Na Quan ◽  
Fei-Feng Wang ◽  
Xia Lu
Keyword(s):  
Asymmetric Synthesis ◽  
Shikimic Acid ◽  
Cyclic Sulfite ◽  
Oseltamivir Phosphate

A novel and high-yielding asymmetric synthesis of oseltamivir phosphate (Tamiflu) starting from (−)-shikimic acid

2012 ◽  
Vol 23 (10) ◽  
pp. 742-747 ◽  
Author(s):  
Liang-Deng Nie ◽  
Wei Ding ◽  
Xiao-Xin Shi ◽  
Na Quan ◽  
Xia Lu
Keyword(s):  
Asymmetric Synthesis ◽  
Shikimic Acid ◽  
Oseltamivir Phosphate

A new and efficient asymmetric synthesis of oseltamivir phosphate (Tamiflu) from d-glucose

Tetrahedron ◽  
2015 ◽  
Vol 71 (16) ◽  
pp. 2393-2399 ◽  
Author(s):  
Boonsong Kongkathip ◽  
Sunisa Akkarasamiyo ◽  
Ngampong Kongkathip
Keyword(s):  
Asymmetric Synthesis ◽  
Oseltamivir Phosphate

A novel azide-free asymmetric synthesis of oseltamivir phosphate (Tamiflu) starting from Roche’s epoxide

2013 ◽  
Vol 24 (11) ◽  
pp. 638-642 ◽  
Author(s):  
Liang-Deng Nie ◽  
Fei-Feng Wang ◽  
Wei Ding ◽  
Xiao-Xin Shi ◽  
Xia Lu
Keyword(s):  
Asymmetric Synthesis ◽  
Oseltamivir Phosphate

Continuous-Flow Synthesis of (–)-Oseltamivir Phosphate (Tamiflu)

Synlett ◽  
2020 ◽  
Vol 31 (19) ◽  
pp. 1925-1929 ◽  
Author(s):  
Paul Watts ◽  
Cloudius R. Sagandira
Keyword(s):  
Residence Time ◽  
Continuous Flow ◽  
Shikimic Acid ◽  
Flow Process ◽  
Flow Synthesis ◽  
Continuous Flow Process ◽  
The Individual ◽  
Total Residence Time ◽  
Oseltamivir Phosphate

Herein the anti-influenza drug (–)-oseltamivir phosphate is prepared in continuous flow from ethyl shikimate with 54% overall yield over nine steps and total residence time of 3.5 min from the individual steps. Although the procedure involved intermediate isolation, the dangerous azide chemistry and intermediates involved were elegantly handled in situ. It is the first continuous-flow process for (–)-oseltamivir phosphate involving azide chemistry and (–)-shikimic acid as precursor.

scholarly journals Cryptomeria japonica (L. F.) D. Don as source of shikimic acid

Revista Fitos ◽  
2020 ◽  
Vol 14 (4) ◽  
pp. 462-468
Author(s):  
Antonio Luiz Cerdeira ◽  
Sonia Claudia Nascimento Queiroz ◽  
Marcus Barifouse Matallo
Keyword(s):  
Influenza Virus ◽  
Glycoside Hydrolase ◽  
Cryptomeria Japonica ◽  
Potent Inhibitor ◽  
Shikimic Acid ◽  
Commercial Production ◽  
Virus H1n1 ◽  
Brand Name ◽  
Reliable Source ◽  
Oseltamivir Phosphate

Oseltamivir phosphate (OSP), marketed under the brand name of Tamiflu®, is a potent inhibitor of viral neuraminidase, a glycoside hydrolase enzyme essential for viral replication. OSP is also important to control influenza virus (H1N1) and is produced mainly from shikimic acid (SA) extracted from plants. The main source of SA is from seeds of I. verum. Alternatives to meet the worldwide demand are necessary. One of this is Cryptomeria japonica. In this study, we found a content of 56.36 mg.kg-1 of SA in dried biomass for C. japonica, while for I.verum, the traditional source, was 96.57 mg.kg-1. Due to the fact of C. japonica is a tree, exploited for commercial production, it can be a renewable and reliable source SA for OSP production.

Streamlined process for the esterification and ketalization of shikimic acid en route to the key precursor for oseltamivir phosphate (Tamiflu™)

2008 ◽  
Vol 10 (7) ◽  
pp. 743 ◽  
Author(s):  
Robert Carr ◽  
Frank Ciccone ◽  
Richard Gabel ◽  
Martin Guinn ◽  
David Johnston ◽  
...  
Keyword(s):  
Shikimic Acid ◽  
Oseltamivir Phosphate

ChemInform Abstract: Asymmetric Synthesis of (-)-4-epi-Shikimic Acid.

ChemInform ◽  
2010 ◽  
Vol 31 (26) ◽  
pp. no-no
Author(s):  
Surachai Pornpakakul ◽  
Robin G. Pritchard ◽  
Richard J. Stoodley
Keyword(s):  
Asymmetric Synthesis ◽  
Shikimic Acid

A Short and Practical Synthesis of Oseltamivir Phosphate (Tamiflu) from (−)-Shikimic Acid†

2009 ◽  
Vol 74 (10) ◽  
pp. 3970-3973 ◽  
Author(s):  
Liang-Deng Nie ◽  
Xiao-Xin Shi ◽  
Kwang Hyok Ko ◽  
Wei-Dong Lu
Keyword(s):  
Shikimic Acid ◽  
Practical Synthesis ◽  
Oseltamivir Phosphate

Asymmetric synthesis of (−)-4-epi-shikimic acid

2000 ◽  
Vol 41 (15) ◽  
pp. 2691-2694 ◽  
Author(s):  
Surachai Pornpakakul ◽  
Robin G Pritchard ◽  
Richard J Stoodley
Keyword(s):  
Asymmetric Synthesis ◽  
Shikimic Acid
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