PMID: 19938847DOI: 10.1021/ol9024716Nov 27, 2009Paper
Efficient formal synthesis of oseltamivir phosphate (Tamiflu) with inexpensive D-ribose as the starting material
Organic Letters
Hiroshi OsatoChristina L L Chai
Abstract
An efficient formal synthesis of oseltamivir phosphate (Tamiflu) has been achieved in 12 steps with use of the inexpensive and highly abundant D-ribose as the starting material. This concise alternative route does not utilize protecting groups and features the introduction of 3-pentylidene ketal as the latent 3-pentyl ether, the use of a highly efficient RCM reaction to form the Tamiflu skeleton, and selective functional group manipulations.
References
Aug 1, 1997·Applied Microbiology and Biotechnology·P De Wulf, E J Vandamme
Apr 13, 2001·The Journal of Organic Chemistry·M Karpf, R Trussardi
Jan 29, 1997·Journal of the American Chemical Society·C U KimR C Stevens
Apr 22, 2006·Science·Martin Enserink
May 11, 2006·Journal of the American Chemical Society·Ying-Yeung YeungE J Corey
May 11, 2006·Journal of the American Chemical Society·Yuhei FukutaMasakatsu Shibasaki
Jul 1, 2006·The Journal of Organic Chemistry·Xin Cong, Zhu-Jun Yao
Oct 20, 2006·Angewandte Chemie·Vittorio Farina, Jack D Brown
Jan 16, 2007·Organic Letters·Tsuyoshi MitaMasakatsu Shibasaki
Jun 28, 2007·Angewandte Chemie·Nobuhiro SatohTohru Fukuyama
Jul 27, 2007·Chemical Communications : Chem Comm·Karen M BromfieldNina Kann
Sep 14, 2007·Journal of the American Chemical Society·Jiun-Jie ShieChi-Huey Wong
Jan 29, 2008·Organic Letters·Nsiama Tienabe KipassaTetsuo Iwagawa
Apr 11, 2008·Angewandte Chemie·Barry M Trost, Ting Zhang
Jun 4, 2008·The Journal of Organic Chemistry·Ulrich ZutterBeat Wirz
Jul 10, 2008·Angewandte Chemie·Jiun-Jie ShieChi-Huey Wong
Nov 19, 2008·Angewandte Chemie·Kenzo YamatsuguMasakatsu Shibasaki
Jan 6, 2009·Angewandte Chemie·Hayato IshikawaYujiro Hayashi
Apr 16, 2009·The Journal of Organic Chemistry·Liang-Deng NieWei-Dong Lu
May 9, 2009·Angewandte Chemie·Bradford SullivanTomas Hudlicky
Jun 23, 2009·Chemical Reviews·Javier Magano
Jul 1, 2009·Angewandte Chemie·Martin Karpf, René Trussardi
❮ Previous
Next ❯
Citations
Dec 5, 2013·Chemical Reviews·Loránd Kiss, Ferenc Fülöp
Nov 16, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Pedro LabordaJosef Voglmeir
May 19, 2010·Angewandte Chemie·Shaolin ZhuDawei Ma
Sep 23, 2010·Chemistry : a European Journal·Hayato IshikawaYujiro Hayashi
Mar 3, 2011·Chemistry : a European Journal·Barry M Trost, Ting Zhang
Dec 21, 2012·Chemistry : a European Journal·Loránd KissFerenc Fülöp
Mar 17, 2012·Beilstein Journal of Organic Chemistry·Melinda NonnFerenc Fülöp
Dec 14, 2016·Environmental Science and Pollution Research International·Chengyi PuPangtuo Bo
Oct 11, 2013·Organic & Biomolecular Chemistry·Chih-An Chen, Jim-Min Fang
Sep 7, 2011·Organic & Biomolecular Chemistry·Milos TrajkovicRadomir N Saicic
Sep 23, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Masahiko Hayashi
Oct 17, 2014·ChemMedChem·Eric K W TamChristina L L Chai
Aug 26, 2020·Tetrahedron·Cloudius R SagandiraPaul Watts
Apr 7, 2010·The Journal of Organic Chemistry·Akio Kamimura, Toshiki Nakano
Apr 17, 2010·The Journal of Organic Chemistry·Jiang WengGui Lu
Apr 16, 2021·The Journal of Organic Chemistry·Virendra K TiwariDavid B Berkowitz
Sep 28, 2010·The Journal of Organic Chemistry·Ji S KoSoo Y Ko
Jun 2, 2011·The Journal of Organic Chemistry·Takanori TanakaMasahiko Hayashi
Jul 25, 2018·Journal of the American Chemical Society·Hongze LiHao Xu
Sep 14, 2012·The Journal of Organic Chemistry·Hong-Se Oh, Han-Young Kang
Oct 20, 2011·The Journal of Organic Chemistry·Lukas WernerJohn Andraos
May 6, 2015·Organic Letters·Jeremy JustJason A Smith
Mar 23, 2013·The Journal of Organic Chemistry·Kaliyamoorthy AlagiriMasakatsu Shibasaki
❮ Previous
Next ❯
Related Concepts
Related Feeds
Antivirals
Antivirals are medications that are used specifically for treating viral infections. Discover the latest research on antivirals here.
Antivirals (ASM)
Antivirals are medications that are used specifically for treating viral infections. Discover the latest research on antivirals here.
Related Papers
The Journal of Organic Chemistry
Ji S KoSoo Y Ko
The Journal of Organic Chemistry
Akio Kamimura, Toshiki Nakano
Chemistry : a European Journal
Jimei MaXue-Wei Liu
The Journal of Organic Chemistry
Vincent E ZiffleDerrick L J Clive
ACS Combinatorial Science
Erhad AscicThomas E Nielsen