Literature DB >> 19601608

An interrupted Fischer indolization approach toward fused indoline-containing natural products.

Ben W Boal1, Alex W Schammel, Neil K Garg.   

Abstract

An efficient method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. Our studies show that the approach will likely be amenable to the synthesis of complex targets, such as the communesin natural products.

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Year:  2009        PMID: 19601608     DOI: 10.1021/ol901383j

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


  16 in total

1.  Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors:  Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

Review 2.  Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.

Authors:  Barry M Trost; Maksim Osipov
Journal:  Chemistry       Date:  2015-09-10       Impact factor: 5.236

3.  Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors:  Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

4.  Flustramine inspired synthesis and biological evaluation of pyrroloindoline triazole amides as novel inhibitors of bacterial biofilms.

Authors:  Cynthia Bunders; John Cavanagh; Christian Melander
Journal:  Org Biomol Chem       Date:  2011-06-15       Impact factor: 3.876

5.  Why do some Fischer indolizations fail?

Authors:  Nihan Çelebi-Ölçüm; Ben W Boal; Alexander D Huters; Neil K Garg; K N Houk
Journal:  J Am Chem Soc       Date:  2011-03-28       Impact factor: 15.419

6.  Synthesis of 3,3'-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates.

Authors:  Arijit A Adhikari; Léa Radal; John D Chisholm
Journal:  Synlett       Date:  2017-07-11       Impact factor: 2.454

7.  Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (-)-2(S)-Cathafoline, and (-)-Aspidophylline A.

Authors:  Jesus Moreno; Elias Picazo; Lucas A Morrill; Joel M Smith; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

8.  Diastereoselective Oxidative C-N/C-O and C-N/C-N Bond Formation Tandems Initiated by Visible Light: Synthesis of Fused N-Arylindolines.

Authors:  Scott A Morris; Theresa H Nguyen; Nan Zheng
Journal:  Adv Synth Catal       Date:  2015-07-14       Impact factor: 5.837

9.  Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.

Authors:  Robert B Susick; Lucas A Morrill; Elias Picazo; Neil K Garg
Journal:  Synlett       Date:  2017       Impact factor: 2.454

10.  Interrupted Fischer indolization approach toward the communesin alkaloids and perophoramidine.

Authors:  Alex W Schammel; Grace Chiou; Neil K Garg
Journal:  Org Lett       Date:  2012-08-20       Impact factor: 6.005

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