Literature DB >> 22475177

TiCl4-promoted tandem carbonyl or imine addition and Friedel-Crafts cyclization: synthesis of benzo-fused oxabicyclooctanes and nonanes.

Arun K Ghosh1, Cuthbert D Martyr, Chun-Xiao Xu.   

Abstract

A new and convenient synthesis of benzo-fused 8-oxabicyclo[3.2.1]octane and 9-oxabicyclo[4.2.1]nonane derivatives are described. The reaction involved a TiCl(4)-mediated tandem carbonyl or imine addition followed by a Friedel-Crafts cyclization to provide these functionalized derivatives in good to excellent yields and high diastereoselectivity.
© 2012 American Chemical Society

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Year:  2012        PMID： 22475177      PMCID： PMC3331910          DOI： 10.1021/ol300494q

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


  9 in total

1.  A short synthesis of (+/-)-eburnamonine.

Authors:  A K Ghosh; R Kawahama
Journal:  J Org Chem       Date:  2000-08-25       Impact factor: 4.354

2.  Highly diastereoselective synthesis of modified nucleosides via an asymmetric multicomponent reaction.

Authors:  Arun K Ghosh; Jorden Kass
Journal:  Chem Commun (Camb)       Date:  2010-01-25       Impact factor: 6.222

3.  New aromatic compounds from the marine mangrove Bruguiera gymnorrhiza.

Authors:  Li Han; Xueshi Huang; Isabel Sattler; Ute Moellmann; Hongzheng Fu; Wenhan Lin; Susanne Grabley
Journal:  Planta Med       Date:  2005-02       Impact factor: 3.352

4.  A stereoselective synthesis of (-)-viridiofungin A utilizing a TiCl(4)-promoted asymmetric multicomponent reaction.

Authors:  Arun K Ghosh; Jorden Kass
Journal:  Org Lett       Date:  2011-12-23       Impact factor: 6.005

5.  Asymmetric multicomponent reactions: diastereoselective synthesis of substituted pyrrolidines and prolines.

Authors:  Arun K Ghosh; Sarang Kulkarni; Chun-Xiao Xu; Phillip E Fanwick
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

6.  Two-step acquisition of resistance to the teicoplanin-gentamicin combination by VanB-type Enterococcus faecalis in vitro and in experimental endocarditis.

Authors:  A Lefort; M Baptista; B Fantin; F Depardieu; M Arthur; C Carbon; P Courvalin
Journal:  Antimicrob Agents Chemother       Date:  1999-03       Impact factor: 5.191

7.  TiCl4-promoted multicomponent reaction: a new entry to functionalized alpha-amino acids.

Authors:  Arun K Ghosh; Chun-Xiao Xu; Sarang S Kulkarni; Donald Wink
Journal:  Org Lett       Date:  2005-01-06       Impact factor: 6.005

8.  An expeditious synthesis of bruguierol A.

Authors:  Francisco J Fañanás; Amadeo Fernández; Deniz Cevic; Félix Rodríguez
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354

9.  Total synthesis and absolute configuration determination of (+)-bruguierol C.

Authors:  Dionicio Martinez Solorio; Michael P Jennings
Journal:  J Org Chem       Date:  2007-07-14       Impact factor: 4.354
  9 in total

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