Literature DB >> 24295135

Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Lindsay M Repka1, Sarah E Reisman.   

Abstract

Pyrroloindoline alkaloids constitute a large family of natural products that has inspired the development of an impressive array of new reactions to prepare the key heterocyclic motif. This synopsis will address catalytic, asymmetric reactions developed to synthesize pyrroloindolines bearing C3a all-carbon quaternary stereocenters. The methods described herein include both transition-metal-catalyzed and organocatalyzed reactions that have been demonstrated to be suitable for the synthesis of the pyrroloindoline framework.

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Year:  2013        PMID: 24295135      PMCID: PMC3905788          DOI: 10.1021/jo4017953

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  59 in total

1.  Highly chemo- and enantioselective synthesis of 3-allyl-3-aryl oxindoles via the direct palladium-catalyzed alpha-arylation of amides.

Authors:  Xinjun Luan; Linglin Wu; Emma Drinkel; Ronaldo Mariz; Michele Gatti; Reto Dorta
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

2.  Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane.

Authors:  Masanari Kimura; Makoto Futamata; Ryutaro Mukai; Yoshinao Tamaru
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

3.  Enantioselective construction of pyrroloindolines catalyzed by chiral phosphoric acids: total synthesis of (-)-debromoflustramine B.

Authors:  Zuhui Zhang; Jon C Antilla
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-17       Impact factor: 15.336

4.  Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes.

Authors:  Barry M Trost; Jean Quancard
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

5.  Bionectins A-C, epidithiodioxopiperazines with anti-MRSA activity, from Bionectra byssicola F120.

Authors:  Chang-Ji Zheng; Chang-Jin Kim; Kyung Sook Bae; Young-Ho Kim; Won-Gon Kim
Journal:  J Nat Prod       Date:  2006-12       Impact factor: 4.050

6.  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

7.  Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade.

Authors:  Shaolin Zhu; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2012-06-22       Impact factor: 15.419

8.  Enantioselective total synthesis of plectosphaeroic acid B.

Authors:  Salman Y Jabri; Larry E Overman
Journal:  J Am Chem Soc       Date:  2013-03-06       Impact factor: 15.419

9.  Palladium-catalyzed alpha-arylation of oxindoles.

Authors:  Matthew J Durbin; Michael C Willis
Journal:  Org Lett       Date:  2008-03-06       Impact factor: 6.005

10.  Nine-step enantioselective total synthesis of (+)-minfiensine.

Authors:  Spencer B Jones; Bryon Simmons; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2009-09-30       Impact factor: 15.419

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  17 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

2.  Lewis Acid Catalyzed Displacement of Trichloroacetimidates in the Synthesis of Functionalized Pyrroloindolines.

Authors:  Arijit A Adhikari; John D Chisholm
Journal:  Org Lett       Date:  2016-08-03       Impact factor: 6.005

3.  Straightforward Access to Hexahydropyrrolo[2,3-b]indole Core by a Regioselective C3-Azo Coupling Reaction of Arenediazonium Compounds with Tryptamines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  European J Org Chem       Date:  2014-06-01

4.  Organocatalytic asymmetric arylation of indoles enabled by azo groups.

Authors:  Liang-Wen Qi; Jian-Hui Mao; Jian Zhang; Bin Tan
Journal:  Nat Chem       Date:  2017-10-02       Impact factor: 24.427

5.  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

6.  Enantioselective total synthesis of (-)-lansai B and (+)-nocardioazines A and B.

Authors:  Haoxuan Wang; Sarah E Reisman
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-28       Impact factor: 15.336

7.  Total Synthesis of Dimeric HPI Alkaloids.

Authors:  Xianfu Shen; Yongyun Zhou; Yongkai Xi; Jingfeng Zhao; Hongbin Zhang
Journal:  Nat Prod Bioprospect       Date:  2016-03-11

8.  Enantio- and diastereoselective diarylmethylation of 1,3-dicarbonyl compounds.

Authors:  Xin Li; Songtao He; Qiuling Song
Journal:  Chem Sci       Date:  2020-05-25       Impact factor: 9.825

9.  Formation of Pyrroloindolines via the Alkylation of Tryptamines with Trichloroacetimidates.

Authors:  Bhaskar D Joshi; John D Chisholm
Journal:  Tetrahedron Lett       Date:  2021-07-01       Impact factor: 2.032

10.  Thiourea-catalyzed enantioselective addition of indoles to pyrones: alkaloid cores with quaternary carbons.

Authors:  Charles S Yeung; Robert E Ziegler; John A Porco; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2014-09-17       Impact factor: 15.419

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