Literature DB >> 29540961

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

Robert B Susick1, Lucas A Morrill1, Elias Picazo1, Neil K Garg1.   

Abstract

This account provides an overview of our laboratory's studies of an unusual variant of the Fischer indolization reaction. We describe the discovery of the so-called 'interrupted Fischer indolization' and the development of the reaction from a methodological standpoint. In addition, our efforts to evaluate and apply this methodology in the context of akuammiline alkaloid total synthesis are discussed.

Entities:  

Keywords:  Fischer indolization; akuammilines; alkaloids; heterocycles; indoles; indolines; natural products; total synthesis

Year:  2017        PMID: 29540961      PMCID: PMC5846481          DOI: 10.1055/s-0036-1588372

Source DB:  PubMed          Journal:  Synlett        ISSN: 0936-5214            Impact factor:   2.454


  70 in total

1.  The second total synthesis of diazonamide A.

Authors:  K C Nicolaou; Paraselli Bheema Rao; Junliang Hao; Mali Venkat Reddy; Gerasimos Rassias; Xianhai Huang; David Y-K Chen; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-17       Impact factor: 15.336

2.  The total synthesis of (+)-dragmacidin F.

Authors:  Neil K Garg; Daniel D Caspi; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-08-11       Impact factor: 15.419

3.  Effects of a modified dye-labeled nucleotide spacer arm on incorporation by thermophilic DNA polymerases.

Authors:  Christopher Lacenere; Meil K Garg; Brian M Stoltz; Stephen R Quake
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2006       Impact factor: 1.381

4.  Total synthesis of (±)-aspidophylline A.

Authors:  Liansuo Zu; Ben W Boal; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-05-18       Impact factor: 15.419

5.  Versatile access to chiral indolines by catalytic asymmetric Fischer indolization.

Authors:  Alberto Martínez; Matthew J Webber; Steffen Müller; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-29       Impact factor: 15.336

6.  Enantioselective, protecting-group-free total synthesis of sarpagine alkaloids--a generalized approach.

Authors:  Sebastian Krüger; Tanja Gaich
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-24       Impact factor: 15.336

7.  Structure, bioactivity and synthesis of natural products with hexahydropyrrolo[2,3-b]indole.

Authors:  Pau Ruiz-Sanchis; Svetlana A Savina; Fernando Albericio; Mercedes Álvarez
Journal:  Chemistry       Date:  2011-01-12       Impact factor: 5.236

8.  Copper(I)-catalyzed aryl or vinyl addition to electron-deficient alkenes cascaded by cationic cyclization.

Authors:  Bing Zhou; Wei Hou; Yaxi Yang; Huijin Feng; Yuanchao Li
Journal:  Org Lett       Date:  2014-02-19       Impact factor: 6.005

9.  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

10.  Total Synthesis of (±)-Strictamine.

Authors:  Weiwu Ren; Qian Wang; Jieping Zhu
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-04       Impact factor: 15.336

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  3 in total

1.  Evaluation of the photodecarbonylation of crystalline ketones for the installation of reverse prenyl groups on the pyrrolidinoindoline scaffold.

Authors:  Jordan J Dotson; Neil K Garg; Miguel A Garcia-Garibay
Journal:  Tetrahedron       Date:  2020-04-10       Impact factor: 2.457

Review 2.  Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step.

Authors:  Bastien Delayre; Qian Wang; Jieping Zhu
Journal:  ACS Cent Sci       Date:  2021-04-08       Impact factor: 14.553

3.  Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies.

Authors:  Elias Picazo; Lucas A Morrill; Robert B Susick; Jesus Moreno; Joel M Smith; Neil K Garg
Journal:  J Am Chem Soc       Date:  2018-05-15       Impact factor: 15.419

  3 in total

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