Literature DB >> 30443083

A Stereoselective Anti-Aldol Route to (3R,3aS,6aR)-Hexahydrofuro[2,3-b] furan-3-ol: A Key Ligand for a New Generation of HIV Protease Inhibitors.

Arun K Ghosh1, Jianfeng Li1, Ramu Sridhar Perali1.   

Abstract

A stereoselective synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol, an important high affinity P2-ligand, in high enantiomeric excess (>99%) is reported. The synthesis features an ester-derived titanium enolate based highly stereoselective anti-aldol reaction as the key step.

Entities:  

Keywords:  aldol reactions; antiviral agents; asymmetric synthesis; chiral auxiliary; fused-ring systems

Year:  2006        PMID： 30443083      PMCID： PMC6233888          DOI： 10.1055/s-2006-942547

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  18 in total

1.  Factors associated with clinical and virological failure in patients receiving a triple therapy including a protease inhibitor.

Authors:  S Grabar; C Pradier; E Le Corfec; R Lancar; C Allavena; M Bentata; P Berlureau; C Dupont; P Fabbro-Peray; I Poizot-Martin; D Costagliola
Journal:  AIDS       Date:  2000-01-28       Impact factor: 4.177

Review 2.  Structure-based design of non-peptide HIV protease inhibitors.

Authors:  A K Ghosh; D Shin; L Swanson; K Krishnan; H Cho; K A Hussain; D E Walters; L Holland; J Buthod
Journal:  Farmaco       Date:  2001 Jan-Feb

3.  Potent HIV protease inhibitors incorporating high-affinity P2-ligands and (R)-(hydroxyethylamino)sulfonamide isostere.

Authors:  A K Ghosh; J F Kincaid; W Cho; D E Walters; K Krishnan; K A Hussain; Y Koo; H Cho; C Rudall; L Holland; J Buthod
Journal:  Bioorg Med Chem Lett       Date:  1998-03-17       Impact factor: 2.823

4.  SYNTHESIS AND OPTICAL RESOLUTION OF HIGH AFFINITY P2-LIGANDS FOR HIV-1 PROTEASE INHIBITORS.

Authors:  Arun K Ghosh; Yan Chen
Journal:  Tetrahedron Lett       Date:  2000-06-14       Impact factor: 2.415

Review 5.  HIV chemotherapy.

Authors:  D D Richman
Journal:  Nature       Date:  2001-04-19       Impact factor: 49.962

6.  Asymmetric synthesis of (-)-tetrahydrolipstatin: an anti-aldol-based strategy.

Authors:  A K Ghosh; S Fidanze
Journal:  Org Lett       Date:  2000-08-10       Impact factor: 6.005

7.  Stereoselective synthesis of pseudopeptide microbial agent AI-77-B.

Authors:  A K Ghosh; A Bischoff; J Cappiello
Journal:  Org Lett       Date:  2001-08-23       Impact factor: 6.005

8.  Stereoselective photochemical 1,3-dioxolane addition to 5-alkoxymethyl-2(5H)-furanone: synthesis of bis-tetrahydrofuranyl ligand for HIV protease inhibitor UIC-94017 (TMC-114).

Authors:  Arun K Ghosh; Sofiya Leshchenko; Marcus Noetzel
Journal:  J Org Chem       Date:  2004-11-12       Impact factor: 4.354

9.  Novel bis-tetrahydrofuranylurethane-containing nonpeptidic protease inhibitor (PI) UIC-94017 (TMC114) with potent activity against multi-PI-resistant human immunodeficiency virus in vitro.

Authors:  Yasuhiro Koh; Hirotomo Nakata; Kenji Maeda; Hiromi Ogata; Geoffrey Bilcer; Thippeswamy Devasamudram; John F Kincaid; Peter Boross; Yuan-Fang Wang; Yunfeng Tie; Patra Volarath; Laquasha Gaddis; Robert W Harrison; Irene T Weber; Arun K Ghosh; Hiroaki Mitsuya
Journal:  Antimicrob Agents Chemother       Date:  2003-10       Impact factor: 5.191

10.  Highly diastereoselective anti-aldol reactions utilizing the titanium enolate of cis-2-arylsulfonamido-1- acenaphthenyl propionate.

Authors:  Arun K Ghosh; Jae-Hun Kim
Journal:  Org Lett       Date:  2003-04-03       Impact factor: 6.005
View more
  1 in total

1.  Nature Inspired Molecular Design: Stereoselective Synthesis of Bicyclic and Polycyclic Ethers for Potent HIV-1 Protease Inhibitors.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  Asian J Org Chem       Date:  2018-06-08       Impact factor: 3.319
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.