Literature DB >> 20178343

Tricyclic alkaloid core structures assembled by a cyclotrimerization-coupled intramolecular nucleophilic substitution reaction.

Andrew L McIver1, Alexander Deiters.   

Abstract

A facile approach to tricyclic alkaloid core structures was developed by sequencing a pyridine-forming [2 + 2 + 2] cyclotrimerization reaction with an intramolecular nucleophilic substitution. This methodology enabled the facile assembly of the spiroindolinone framework of citrinadins A and B, and cyclopiamine B.

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Year:  2010        PMID： 20178343     DOI： 10.1021/ol100177u

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


  10 in total

Review 1.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

2.  Synthetic studies toward the citrinadin A and B core architecture.

Authors:  Devon A Mundal; Richmond Sarpong
Journal:  Org Lett       Date:  2013-09-19       Impact factor: 6.005

3.  Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.

Authors:  Zhiguo Bian; Christopher C Marvin; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

4.  Concise, stereocontrolled synthesis of the citrinadin B core architecture.

Authors:  Carlos A Guerrero; Erik J Sorensen
Journal:  Org Lett       Date:  2011-09-06       Impact factor: 6.005

5.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

6.  Mechanistic Evaluation of the Ni(IPr)2-Catalyzed Cycloaddition of Alkynes and Nitriles to Afford Pyridines: Evidence for the Formation of a Key η1-Ni(IPr)2(RCN) Intermediate.

Authors:  Ryan M Stolley; Hung A Duong; Janis Louie
Journal:  Organometallics       Date:  2013-09-09       Impact factor: 3.876

7.  Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride.

Authors:  Subrata Kumar Chaudhuri; Manabendra Saha; Amit Saha; Sanjay Bhar
Journal:  Beilstein J Org Chem       Date:  2010-09-02       Impact factor: 2.883

8.  Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael-Henry cascade reactions.

Authors:  Yonglei Du; Jian Li; Kerong Chen; Chenglin Wu; Yu Zhou; Hong Liu
Journal:  Beilstein J Org Chem       Date:  2017-07-07       Impact factor: 2.883

9.  Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins.

Authors:  Zhiwen Liu; Fanglong Zhao; Boyang Zhao; Jie Yang; Joseph Ferrara; Banumathi Sankaran; B V Venkataram Prasad; Biki Bapi Kundu; George N Phillips; Yang Gao; Liya Hu; Tong Zhu; Xue Gao
Journal:  Nat Commun       Date:  2021-07-06       Impact factor: 14.919

10.  Enantioselective total syntheses of citrinadins A and B. Stereochemical revision of their assigned structures.

Authors:  Zhiguo Bian; Christopher C Marvin; Martin Pettersson; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2014-09-29       Impact factor: 15.419
  10 in total

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