Literature DB >> 21830283

The Pictet-Spengler reaction in nature and in organic chemistry.

Joachim Stöckigt1, Andrey P Antonchick, Fangrui Wu, Herbert Waldmann.   

Abstract

Alkaloids are an important class of natural products that are widely distributed in nature and produced by a large variety of organisms. They have a wide spectrum of biological activity and for many years were used in folk medicine. These days, alkaloids also have numerous applications in medicine as therapeutic agents. The importance of these natural products in inspiring drug discovery programs is proven and, therefore, their continued synthesis is of significant interest. The condensation discovered by Pictet and Spengler is the most important method for the synthesis of alkaloid scaffolds. The power of this synthesis method has been convincingly proven in the construction of stereochemicaly and structurally complex alkaloids.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID: 21830283     DOI: 10.1002/anie.201008071

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  71 in total

1.  Palladium-catalyzed regio- and stereoselective γ-arylation of tertiary allylic amines: identification of potent adenylyl cyclase inhibitors.

Authors:  Zhishi Ye; Tarsis F Brust; Val J Watts; Mingji Dai
Journal:  Org Lett       Date:  2015-02-10       Impact factor: 6.005

Review 2.  Non-enzymatic molecular damage as a prototypic driver of aging.

Authors:  Alexey Golubev; Andrew D Hanson; Vadim N Gladyshev
Journal:  J Biol Chem       Date:  2017-03-06       Impact factor: 5.157

3.  Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones.

Authors:  Joseph J Badillo; Abel Silva-García; Benjamin H Shupe; James C Fettinger; Annaliese K Franz
Journal:  Tetrahedron Lett       Date:  2011-10-26       Impact factor: 2.415

4.  Catalytic stereoselective synthesis of diverse oxindoles and spirooxindoles from isatins.

Authors:  Jacob P MacDonald; Joseph J Badillo; Gary E Arevalo; Abel Silva-García; Annaliese K Franz
Journal:  ACS Comb Sci       Date:  2012-04-02       Impact factor: 3.784

Review 5.  Biosynthesis of fungal indole alkaloids.

Authors:  Wei Xu; Diego J Gavia; Yi Tang
Journal:  Nat Prod Rep       Date:  2014-10       Impact factor: 13.423

Review 6.  Click chemistry in complex mixtures: bioorthogonal bioconjugation.

Authors:  Craig S McKay; M G Finn
Journal:  Chem Biol       Date:  2014-09-18

Review 7.  The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems.

Authors:  Chia-I Lin; Reid M McCarty; Hung-Wen Liu
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-14       Impact factor: 15.336

8.  Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction.

Authors:  Rebekka S Klausen; C Rose Kennedy; Alan M Hyde; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419

9.  MHTP, 2-Methoxy-4-(7-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl) phenol, a Synthetic Alkaloid, Induces IFN-γ Production in Murine Model of Ovalbumin-Induced Pulmonary Allergic Inflammation.

Authors:  Laércia K D Paiva Ferreira; Larissa A M Paiva Ferreira; Adriano Francisco Alves; Fagner Carvalho Leite; Luiz A de Araújo Silva; Giciane Carvalho Vieira; Luís Cezar Rodrigues; Marcia Regina Piuvezam
Journal:  Inflammation       Date:  2018-12       Impact factor: 4.092

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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