Literature DB >> 23772095

Enantioselective cyclization of enamide-ynes and application to the synthesis of the kopsifoline core.

Britton K Corkey1, Stephen T Heller, Yi-Ming Wang, F Dean Toste.   

Abstract

We report the palladium-catalyzed enantioselective cyclization of 1,6-enamidynes to form spirocyclic ring systems. We applied this methodology to the concise synthesis of the skeletal core of the kopsifoline alkaloids.

Entities:  

Keywords:  Palladium catalysis; electrophilic activation; enantioselective synthesis; natural product synthesis; spirocyclization

Year:  2013        PMID： 23772095      PMCID： PMC3678774          DOI： 10.1016/j.tet.2013.02.091

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  32 in total

1.  Transition Metal-Catalyzed Carbocyclizations in Organic Synthesis.

Authors:  Iwao Ojima; Maria Tzamarioudaki; Zhaoyang Li; Robert J. Donovan
Journal:  Chem Rev       Date:  1996-03-28       Impact factor: 60.622

Review 2.  Cascade reactions in total synthesis.

Authors:  K C Nicolaou; David J Edmonds; Paul G Bulger
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-06       Impact factor: 15.336

3.  Mechanistic dichotomy in CpRu(CH(3)CN)(3)PF(6) catalyzed enyne cycloisomerizations.

Authors:  Barry M Trost; F Dean Toste
Journal:  J Am Chem Soc       Date:  2002-05-08       Impact factor: 15.419

4.  Catalytic enantioselective Conia-ene reaction.

Authors:  Britton K Corkey; F Dean Toste
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

5.  A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

6.  Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

Authors:  Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Novel rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift.

Authors:  Xiaofeng Tong; Zhaoguo Zhang; Xumu Zhang
Journal:  J Am Chem Soc       Date:  2003-05-28       Impact factor: 15.419

8.  Ns strategies: a highly versatile synthetic method for amines.

Authors:  Toshiyuki Kan; Tohru Fukuyama
Journal:  Chem Commun (Camb)       Date:  2003-11-25       Impact factor: 6.222

9.  Gold(I)-catalyzed regioselective cyclizations of silyl ketene amides and carbamates with alkynes.

Authors:  Ellen C Minnihan; Steven L Colletti; F Dean Toste; Hong C Shen
Journal:  J Org Chem       Date:  2007-07-11       Impact factor: 4.354

Review 10.  Strategies for the enantioselective synthesis of spirooxindoles.

Authors:  Nicolas R Ball-Jones; Joseph J Badillo; Annaliese K Franz
Journal:  Org Biomol Chem       Date:  2012-05-14       Impact factor: 3.876
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  4 in total

1.  Development of catalysts and ligands for enantioselective gold catalysis.

Authors:  Yi-Ming Wang; Aaron D Lackner; F Dean Toste
Journal:  Acc Chem Res       Date:  2013-11-14       Impact factor: 22.384

2.  Modular synthesis and transition metal-free alkynylation/alkenylation of Castagnoli-Cushman-derived N,O- and N,S-heterocyclic vinyl chlorides.

Authors:  Timothy K Beng; Abdikani Omar Farah; Victoria Shearer
Journal:  RSC Adv       Date:  2020-10-07       Impact factor: 4.036

3.  Total syntheses of (-)-kopsifoline D and (-)-deoxoapodine: divergent total synthesis via late-stage key strategic bond formation.

Authors:  Kiyoun Lee; Dale L Boger
Journal:  J Am Chem Soc       Date:  2014-02-17       Impact factor: 15.419

4.  Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade.

Authors:  James A Rossi-Ashton; Aimee K Clarke; Richard J K Taylor; William P Unsworth
Journal:  Org Lett       Date:  2020-01-15       Impact factor: 6.005
  4 in total

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