Literature DB >> 20148531

A concise enantioselective synthesis of (-)-ranirestat.

Barry M Trost1, Maksim Osipov, Guangbin Dong.   

Abstract

A concise, enantioselective synthesis of the potent aldose reductase inhibitor ranirestat (1) is reported. The synthesis was accomplished employing inexpensive, commercially available starting materials. A palladium-catalyzed asymmetric allylic alkylation (Pd-AAA) of malonate 4 was utilized as a key transformation to construct the tetrasubstituted chiral center in the target.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20148531      PMCID： PMC2850125          DOI： 10.1021/ol100167w

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  18 in total

1.  Highly regio- and enantioselective Pd-catalyzed allylic alkylation and amination of monosubstituted allylic acetates with novel ferrocene P,N-ligands.

Authors:  S L You; X Z Zhu; Y M Luo; X L Hou; L X Dai
Journal:  J Am Chem Soc       Date:  2001-08-01       Impact factor: 15.419

2.  Markovnikov alkyne hydrosilylation catalyzed by ruthenium complexes.

Authors:  B M Trost; Z T Ball
Journal:  J Am Chem Soc       Date:  2001-12-19       Impact factor: 15.419

3.  En route to an efficient catalytic asymmetric synthesis of AS-3201.

Authors:  Tomoyuki Mashiko; Keiichi Hara; Daisuke Tanaka; Yuji Fujiwara; Naoya Kumagai; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2007-08-28       Impact factor: 15.419

4.  Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: efficient and general trans addition.

Authors:  Barry M Trost; Zachary T Ball
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

5.  Palladium asymmetric allylic alkylation of prochiral nucleophiles: horsfiline.

Authors:  Barry M Trost; Megan K Brennan
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

6.  Global burden of diabetes, 1995-2025: prevalence, numerical estimates, and projections.

Authors:  H King; R E Aubert; W H Herman
Journal:  Diabetes Care       Date:  1998-09       Impact factor: 19.112

7.  Improved procedure for the oxidative cleavage of olefins by OsO4-NaIO4.

Authors:  Wensheng Yu; Yan Mei; Ying Kang; Zhengmao Hua; Zhendong Jin
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

8.  Iodomesitylene-catalyzed oxidative cleavage of carbon-carbon double and triple bonds using m-chloroperbenzoic acid as a terminal oxidant.

Authors:  Kazunori Miyamoto; Yoshihisa Sei; Kentaro Yamaguchi; Masahito Ochiai
Journal:  J Am Chem Soc       Date:  2009-02-04       Impact factor: 15.419

9.  Novel, highly potent aldose reductase inhibitors: (R)-(-)-2-(4-bromo-2-fluorobenzyl)-1,2,3,4- tetrahydropyrrolo[1,2-a]pyrazine -4-spiro-3'-pyrrolidine-1,2',3,5'-tetrone (AS-3201) and its congeners.

Authors:  T Negoro; M Murata; S Ueda; B Fujitani; Y Ono; A Kuromiya; M Komiya; K Suzuki; J Matsumoto
Journal:  J Med Chem       Date:  1998-10-08       Impact factor: 7.446

10.  Enantioselective cyclization/hydrosilylation of 1,6-enynes catalyzed by a cationic rhodium bis(phosphine) complex.

Authors:  Harinath Chakrapani; Cong Liu; Ross A Widenhoefer
Journal:  Org Lett       Date:  2003-01-23       Impact factor: 6.005
View more
  4 in total

Review 1.  Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids.

Authors:  Beau P Pritchett; Brian M Stoltz
Journal:  Nat Prod Rep       Date:  2018-06-20       Impact factor: 13.423

2.  Gold catalyzed cyclization of alkyne-tethered dihydropyrimidones.

Authors:  Lauren E Brown; Peng Dai; John A Porco; Scott E Schaus
Journal:  Org Lett       Date:  2011-07-13       Impact factor: 6.005

3.  Metal Catalyzed Allylic Alkylation: Its Development in the Trost Laboratories.

Authors:  Barry M Trost
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

4.  Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8-DMSO: application to the synthesis of vernakalant.

Authors:  Dnyaneshwar N Garad; Subhash D Tanpure; Santosh B Mhaske
Journal:  Beilstein J Org Chem       Date:  2015-06-12       Impact factor: 2.883
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.