Literature DB >> 24032694

Construction of vicinal all-carbon quaternary stereocenters by catalytic asymmetric alkylation reaction of 3-bromooxindoles with 3-substituted indoles: total synthesis of (+)-perophoramidine.

Hailong Zhang1, Liang Hong, Hong Kang, Rui Wang.   

Abstract

Highly congested vicinal all-carbon quaternary stereocenters were generated via catalytic asymmetric alkylation reaction of 3-bromooxindoles with 3-substituted indoles. These catalytic reactions proceeded in excellent yields with a broad scope on either reaction partner, and with outstanding diastereo- and enantiocontrol. The newly developed method led to the total synthesis of (+)-perophoramidine in a highly efficient manner.

Entities:  

Mesh:

Substances:

Year:  2013        PMID: 24032694     DOI: 10.1021/ja408336v

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  18 in total

Review 1.  Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.

Authors:  Barry M Trost; Maksim Osipov
Journal:  Chemistry       Date:  2015-09-10       Impact factor: 5.236

2.  Exploiting translational stalling peptides in an effort to extend azithromycin interaction within the prokaryotic ribosome nascent peptide exit tunnel.

Authors:  Arren Z Washington; Subhasish Tapadar; Alex George; Adegboyega K Oyelere
Journal:  Bioorg Med Chem       Date:  2015-05-06       Impact factor: 3.641

3.  Stereochemical evaluation of bis(phosphine) copper catalysts for the asymmetric alkylation of 3-bromooxindoles with α-arylated malonate esters.

Authors:  Chung Whan Lee; Seo-Jung Han; Scott C Virgil; Brian M Stoltz
Journal:  Tetrahedron       Date:  2015-06-03       Impact factor: 2.457

4.  Catalytic enantioselective synthesis of quaternary carbon stereocentres.

Authors:  Kyle W Quasdorf; Larry E Overman
Journal:  Nature       Date:  2014-12-11       Impact factor: 49.962

5.  Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-11       Impact factor: 15.336

6.  Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution.

Authors:  Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2014-04-29       Impact factor: 15.419

7.  Ligand-enabled multiple absolute stereocontrol in metal-catalysed cycloaddition for construction of contiguous all-carbon quaternary stereocentres.

Authors:  Kohsuke Ohmatsu; Naomichi Imagawa; Takashi Ooi
Journal:  Nat Chem       Date:  2013-11-24       Impact factor: 24.427

8.  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

9.  A diastereodivergent synthetic strategy for the syntheses of communesin F and perophoramidine.

Authors:  Seo-Jung Han; Florian Vogt; Shyam Krishnan; Jeremy A May; Michele Gatti; Scott C Virgil; Brian M Stoltz
Journal:  Org Lett       Date:  2014-06-09       Impact factor: 6.005

Review 10.  Catalytic enantioselective construction of vicinal quaternary carbon stereocenters.

Authors:  Feng Zhou; Lei Zhu; Bo-Wen Pan; Yang Shi; Yun-Lin Liu; Jian Zhou
Journal:  Chem Sci       Date:  2020-07-28       Impact factor: 9.825

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.