Literature DB >> 22575071

Total syntheses of chelidonine and norchelidonine via an enamide-benzyne-[2 + 2] cycloaddition cascade.

Zhi-Xiong Ma1, John B Feltenberger, Richard P Hsung.   

Abstract

Total syntheses of chelidonine and norchelidonine featuring an enamide-benzyne-[2 + 2] cycloaddition initiated cascade is described. The cascade includes a pericyclic ring-opening and intramolecular Diels-Alder reaction.

Entities:  

Mesh:

Substances:

Year:  2012        PMID: 22575071      PMCID: PMC3366029          DOI: 10.1021/ol300967a

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


  33 in total

1.  The total synthesis of (+/-)-pumiliotoxin-C.

Authors:  W Oppolzer; W Fröstl
Journal:  Helv Chim Acta       Date:  1975-03-12       Impact factor: 2.164

2.  C(1)-symmetric sulfoximines as ligands in copper-catalyzed asymmetric Mukaiyama-type aldol reactions.

Authors:  Martin Langner; Carsten Bolm
Journal:  Angew Chem Int Ed Engl       Date:  2004-11-12       Impact factor: 15.336

3.  A concise total synthesis of (-)-quinocarcin via aryne annulation.

Authors:  Kevin M Allan; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2008-12-24       Impact factor: 15.419

Review 4.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

Authors:  Gwilherm Evano; Nicolas Blanchard; Mathieu Toumi
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

5.  The benzyne Fischer-indole reaction.

Authors:  Donald McAusland; Sangwon Seo; Didier G Pintori; Jonathan Finlayson; Michael F Greaney
Journal:  Org Lett       Date:  2011-06-14       Impact factor: 6.005

6.  Enantioselective total synthesis of (+)-homochelidonine by a PdII-catalyzed asymmetric ring-opening reaction of a meso-azabicyclic alkene with an aryl boronic acid.

Authors:  Helen A McManus; Matthew J Fleming; Mark Lautens
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

7.  Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

Authors:  John B Feltenberger; Ryuji Hayashi; Yu Tang; Eric S C Babiash; Richard P Hsung
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

8.  Copper-catalyzed coupling of amides and carbamates with vinyl halides.

Authors:  Lei Jiang; Gabriel E Job; Artis Klapars; Stephen L Buchwald
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

9.  Copper-catalyzed alkyne-aryne and alkyne-alkene-aryne coupling reactions.

Authors:  Chunsong Xie; Leifang Liu; Yuhong Zhang; Peixin Xu
Journal:  Org Lett       Date:  2008-05-17       Impact factor: 6.005

10.  CuI/N,N-dimethylglycine-catalyzed coupling of vinyl halides with amides or carbamates.

Authors:  Xianhua Pan; Qian Cai; Dawei Ma
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005

View more
  5 in total

1.  A highly regio- and stereoselective synthesis of α-fluorinated imides via fluorination of chiral enamides.

Authors:  Yan-Shuang Xu; Yu Tang; He-Jing Feng; Ji-Tian Liu; Richard P Hsung
Journal:  Org Lett       Date:  2015-01-12       Impact factor: 6.005

2.  Cycloaddition of Arynes and Cyclic Enol Ethers as a Platform for Access to Stereochemically Defined 1,2-Disubstituted Benzocyclobutenes.

Authors:  Vijayendar R Yedulla; Padmanava Pradhan; Lijia Yang; Mahesh K Lakshman
Journal:  European J Org Chem       Date:  2014-12-22

3.  Palladium-Catalyzed Access to Benzocyclobutenone-Derived Ketonitrones via C(sp2)-H Functionalization.

Authors:  Jakub Brześkiewicz; Rafał Loska
Journal:  Org Lett       Date:  2022-05-25       Impact factor: 6.072

4.  Versatile Dibenzothio[seleno]phenes via Hexadehydro-Diels-Alder Domino Cyclization.

Authors:  Baohua Liu; Qiong Hu; Yinshan Wen; Bo Fang; Xiaoliang Xu; Yimin Hu
Journal:  Front Chem       Date:  2019-05-24       Impact factor: 5.221

5.  Alkane desaturation by concerted double hydrogen atom transfer to benzyne.

Authors:  Dawen Niu; Patrick H Willoughby; Brian P Woods; Beeraiah Baire; Thomas R Hoye
Journal:  Nature       Date:  2013-09-26       Impact factor: 49.962

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.