Literature DB >> 23714013

Palladium-catalyzed synthesis of N-tert-prenylindoles.

Kirsten F Johnson1, Ryan Van Zeeland, Levi M Stanley.   

Abstract

Palladium-catalyzed N-tert-prenylations of indoles, tricarbonylchromium-activated indoles, and indolines that occur in high yields (up to 94%) with high tert-prenyl-to-n-prenyl selectivity (up to 12:1) are reported.

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Year:  2013        PMID： 23714013      PMCID： PMC3721965          DOI： 10.1021/ol4011344

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


  30 in total

1.  Primary tert- and sec-allylamines via palladium-catalyzed hydroamination and allylic substitution with hydrazine and hydroxylamine derivatives.

Authors:  Adam M Johns; Zhijian Liu; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 2.  Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis.

Authors:  Shu-Ming Li
Journal:  Nat Prod Rep       Date:  2009-11-19       Impact factor: 13.423

3.  Synthesis of notoamide J: a potentially pivotal intermediate in the biosynthesis of several prenylated indole alkaloids.

Authors:  Jennifer M Finefield; Robert M Williams
Journal:  J Org Chem       Date:  2010-05-07       Impact factor: 4.354

4.  A new approach to enantiopure C3-symmetric molecules.

Authors:  M Paola Castaldi; Susan E Gibson; Matthew Rudd; Andrew J P White
Journal:  Chemistry       Date:  2005-12-16       Impact factor: 5.236

5.  Biochemical characterization of NotB as an FAD-dependent oxidase in the biosynthesis of notoamide indole alkaloids.

Authors:  Shengying Li; Jennifer M Finefield; James D Sunderhaus; Timothy J McAfoos; Robert M Williams; David H Sherman
Journal:  J Am Chem Soc       Date:  2011-12-28       Impact factor: 15.419

Review 6.  Indole prenylation in alkaloid synthesis.

Authors:  Thomas Lindel; Nils Marsch; Santosh Kumar Adla
Journal:  Top Curr Chem       Date:  2012

7.  Studies on the biosynthesis of the notoamides: synthesis of an isotopomer of 6-hydroxydeoxybrevianamide E and biosynthetic incorporation into notoamide J.

Authors:  Jennifer M Finefield; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  J Org Chem       Date:  2011-06-28       Impact factor: 4.354

8.  Asymmetric total syntheses of (+)- and (-)-versicolamide B and biosynthetic implications.

Authors:  Kenneth A Miller; Sachiko Tsukamoto; Robert M Williams
Journal:  Nat Chem       Date:  2009-04       Impact factor: 24.427

9.  Iridium-catalyzed regio- and enantioselective N-allylation of indoles.

Authors:  Levi M Stanley; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Complexity generation in fungal peptidyl alkaloid biosynthesis: a two-enzyme pathway to the hexacyclic MDR export pump inhibitor ardeemin.

Authors:  Stuart W Haynes; Xue Gao; Yi Tang; Christopher T Walsh
Journal:  ACS Chem Biol       Date:  2013-02-06       Impact factor: 5.100
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  3 in total

1.  Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.

Authors:  Faben A Cruz; Yamin Zhu; Quentin D Tercenio; Zengming Shen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

2.  Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation.

Authors:  Alexander J Grenning; Jonathan H Boyce; John A Porco
Journal:  J Am Chem Soc       Date:  2014-08-07       Impact factor: 15.419

Review 3.  Recent Developments on the Synthesis and Bioactivity of Ilamycins/Rufomycins and Cyclomarins, Marine Cyclopeptides That Demonstrate Anti-Malaria and Anti-Tuberculosis Activity.

Authors:  Uli Kazmaier; Lukas Junk
Journal:  Mar Drugs       Date:  2021-08-03       Impact factor: 5.118
  3 in total

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