Literature DB >> 26085695

Selective synthesis of either enantiomer of an anti-breast cancer agent via a common enantioenriched intermediate.

Aaron George Johnson1, Marissa M Tranquilli1, Michael R Harris1, Elizabeth R Jarvo1.   

Abstract

A stereoselective synthesis of a bioactive triarylmethane is described. Key to the synthesis is a nickel-catalyzed Suzuki-Miyaura coupling which proceeds with retention at the benzylic center. This method is complementary to our previously reported nickel-catalyzed Kumada coupling which proceeds with inversion. Together, the two methods allow for efficient access to either enantiomer of biologically relevant triarylmethanes from a common enantioenriched intermediate.

Entities:  

Keywords:  anti-cancer agent; cross-coupling; nickel; stereospecific; triarylmethane

Year:  2015        PMID: 26085695      PMCID: PMC4465125          DOI: 10.1016/j.tetlet.2015.02.121

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  30 in total

1.  Effect of substituents on diarylmethanes for antitubercular activity.

Authors:  Gautam Panda; Maloy Kumar Parai; Sajal Kumar Das; Manish Sinha; Vinita Chaturvedi; Anil K Srivastava; Y S Manju; Anil N Gaikwad; Sudhir Sinha
Journal:  Eur J Med Chem       Date:  2006-11-15       Impact factor: 6.514

2.  Substituted phenanthrenes with basic amino side chains: a new series of anti-breast cancer agents.

Authors:  Ajay Kumar Srivastava; Ramesh Sharma; Rajeev Mishra; Anil Kumar Balapure; Puvvada S R Murthy; Gautam Panda
Journal:  Bioorg Med Chem       Date:  2005-10-24       Impact factor: 3.641

3.  A copper(II)-catalyzed aza-Friedel-Crafts reaction of N-(2-pyridyl)sulfonyl aldimines: synthesis of unsymmetrical diaryl amines and triaryl methanes.

Authors:  Jorge Esquivias; Ramón Gómez Arrayás; Juan C Carretero
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-16       Impact factor: 15.336

4.  Palladium-catalyzed C(sp3)-H arylation of diarylmethanes at room temperature: synthesis of triarylmethanes via deprotonative-cross-coupling processes.

Authors:  Jiadi Zhang; Ana Bellomo; Andrea D Creamer; Spencer D Dreher; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419

5.  Suzuki-Miyaura cross-coupling reactions of benzyl halides with potassium aryltrifluoroborates.

Authors:  Gary A Molander; Maxwell D Elia
Journal:  J Org Chem       Date:  2006-11-24       Impact factor: 4.354

6.  Chiral Brønsted acid-catalyzed Friedel-Crafts alkylation of electron-rich arenes with in situ-generated ortho-quinone methides: highly enantioselective synthesis of diarylindolylmethanes and triarylmethanes.

Authors:  Satyajit Saha; Santosh Kumar Alamsetti; Christoph Schneider
Journal:  Chem Commun (Camb)       Date:  2015-01-28       Impact factor: 6.222

7.  Enantioselective synthesis of triarylmethanes by chiral imidodiphosphoric acids catalyzed Friedel-Crafts reactions.

Authors:  Ming-Hua Zhuo; Yi-Jun Jiang; Yan-Sen Fan; Yang Gao; Song Liu; Suoqin Zhang
Journal:  Org Lett       Date:  2014-02-03       Impact factor: 6.005

8.  Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts.

Authors:  Antonio L Braga; Marcio W Paixão; Bernhard Westermann; Paulo H Schneider; Ludger A Wessjohann
Journal:  J Org Chem       Date:  2008-03-04       Impact factor: 4.354

9.  Modular synthesis of triarylmethanes through palladium-catalyzed sequential arylation of methyl phenyl sulfone.

Authors:  Masakazu Nambo; Cathleen M Crudden
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-04       Impact factor: 15.336

10.  Diaryl naphthyl methanes a novel class of anti-implantation agents.

Authors:  Neeta Srivastava; S Ray; M M Singh; Anila Dwivedi; Atul Kumar
Journal:  Bioorg Med Chem       Date:  2004-03-01       Impact factor: 3.641

View more
  6 in total

1.  Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.

Authors:  Shuo-Qing Zhang; Buck L H Taylor; Chong-Lei Ji; Yuan Gao; Michael R Harris; Luke E Hanna; Elizabeth R Jarvo; K N Houk; Xin Hong
Journal:  J Am Chem Soc       Date:  2017-09-07       Impact factor: 15.419

2.  Stereospecific Cross-Coupling Reactions Provide Conformationally-Biased Arylalkanes with Anti-Leukemia Activity.

Authors:  Amberly B Sanford; Emily J Tollefson; Elizabeth R Jarvo
Journal:  Isr J Chem       Date:  2019-09-06       Impact factor: 3.333

3.  Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

Authors:  Sarah M Pound; Mary P Watson
Journal:  Chem Commun (Camb)       Date:  2018-10-30       Impact factor: 6.222

4.  Stereospecific nickel-catalyzed cross-coupling reactions of benzylic ethers and esters.

Authors:  Emily J Tollefson; Luke E Hanna; Elizabeth R Jarvo
Journal:  Acc Chem Res       Date:  2015-07-21       Impact factor: 22.384

5.  Nickel-Catalyzed Arylation of Heteroaryl-containing Diarylmethanes: Exceptional Reactivity of the Ni(NIXANTPHOS)-based Catalyst.

Authors:  Xinyu Cao; Sheng-Chun Sha; Minyan Li; Byeong-Seon Kim; Catherine Morgan; Rudan Huang; Xiaodong Yang; Patrick J Walsh
Journal:  Chem Sci       Date:  2015-10-26       Impact factor: 9.825

6.  Harnessing C-O Bonds in Stereoselective Cross-Coupling and Cross-Electrophile Coupling Reactions.

Authors:  Amberly B Sanford; Elizabeth R Jarvo
Journal:  Synlett       Date:  2020-11-27       Impact factor: 2.454

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.