Literature DB >> 19824722

A tandem cascade cyclization-electrophilic aromatic substitution: application in the total synthesis of (+)-angelichalcone.

Joseph J Topczewski1, Michael P Callahan, Jeffrey D Neighbors, David F Wiemer.   

Abstract

When cascade cyclizations initiated by Lewis acid-mediated opening of an epoxide are terminated through reaction with a MOM-protected phenol, a tandem electrophilic aromatic substitution can be obtained. This highly regioselective tandem process has been employed in the first synthesis of (+)-angelichalcone.

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Year:  2009        PMID： 19824722     DOI： 10.1021/ja906468v

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


  8 in total

1.  REGIOSELECTIVE MULTICOMPONENT DOMINO REACTIONS PROVIDING RAPID AND EFFICIENT ROUTES TO FUSED ACRIDINES.

Authors:  Jin-Peng Zhang; Wei Fan; Jie Ding; Bo Jiang; Shu-Jiang Tu; Guigen Li
Journal:  Heterocycles       Date:  2013-12-17       Impact factor: 0.831

2.  Formal [4+3] epoxide cascade reaction via a complementary ambiphilic pairing strategy.

Authors:  Alan Rolfe; Thiwanka B Samarakoon; Paul R Hanson
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

3.  Electrophilic aromatic prenylation via cascade cyclization.

Authors:  John G Kodet; Joseph J Topczewski; Kevyn D Gardner; David F Wiemer
Journal:  Tetrahedron       Date:  2013-10-04       Impact factor: 2.457

4.  Selective opioid growth factor receptor antagonists based on a stilbene isostere.

Authors:  David P Stockdale; Michelle B Titunick; Jessica M Biegler; Jessie L Reed; Alyssa M Hartung; David F Wiemer; Patricia J McLaughlin; Jeffrey D Neighbors
Journal:  Bioorg Med Chem       Date:  2017-06-27       Impact factor: 3.641

5.  Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.

Authors:  Joseph J Topczewski; John G Kodet; David F Wiemer
Journal:  J Org Chem       Date:  2011-01-12       Impact factor: 4.354

6.  Synthesis of heterocycles via Pd-ligand controlled cyclization of 2-chloro-N-(2-vinyl)aniline: preparation of carbazoles, indoles, dibenzazepines, and acridines.

Authors:  Dmitry Tsvelikhovsky; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

7.  Highly selective domino multicyclizations for forming polycyclic fused acridines and azaheterocyclic skeletons.

Authors:  Bo Jiang; Xue Wang; Hai-Wei Xu; Man-Su Tu; Shu-Jiang Tu; Guigen Li
Journal:  Org Lett       Date:  2013-03-18       Impact factor: 6.005

Review 8.  Schweinfurthins A-Q: isolation, synthesis, and biochemical properties.

Authors:  Dipesh S Harmalkar; Jyotirling R Mali; Aneesh Sivaraman; Yongseok Choi; Kyeong Lee
Journal:  RSC Adv       Date:  2018-06-08       Impact factor: 4.036
  8 in total

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