Literature DB >> 20486685

Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction.

Tejas P Pathak1, Keith M Gligorich, Bryan E Welm, Matthew S Sigman.   

Abstract

A unique alkene difunctionalization reaction that allows rapid construction of molecular complexity around the biologically relevant indole framework has been developed. The reaction proceeds with up to 87% yield, 99:1 er, and >20:1 dr. Evaluation of several of the compounds revealed promising anticancer activity against MCF-7 cells.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20486685      PMCID： PMC2896870          DOI： 10.1021/ja103472a

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  9 in total

1.  Biomimetic synthesis of the pyrrolobenzoxazine core of paeciloxazine.

Authors:  Dirk Schwaebisch; Kirill Tchabanenko; Robert M Adlington; Andrew M Cowley; Jack E Baldwin
Journal:  Chem Commun (Camb)       Date:  2004-10-25       Impact factor: 6.222

Review 2.  Simple indole alkaloids and those with a non-rearranged monoterpenoid unit.

Authors:  Masanori Somei; Fumio Yamada
Journal:  Nat Prod Rep       Date:  2005-01-10       Impact factor: 13.423

Review 3.  It all began with an error: the nomofungin/communesin story.

Authors:  Peter Siengalewicz; Tanja Gaich; Johann Mulzer
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Catalytic functionalization of indoles in a new dimension.

Authors:  Marco Bandini; Astrid Eichholzer
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Discovery through total synthesis: a retrospective on the himastatin problem.

Authors:  T M Kamenecka; S J Danishefsky
Journal:  Chemistry       Date:  2001-01-05       Impact factor: 5.236

6.  The reaction of derivatives of tryptophan, tryptamine, and other indoles with 2-hydroxy-5-nitrobenzyl bromide (Koshland's reagent).

Authors:  T F Spande; M Wilchek; B Witkop
Journal:  J Am Chem Soc       Date:  1968-06-05       Impact factor: 15.419

7.  The reaction of Koshland's protein reagent with tryptophan.

Authors:  B G McFarland; Y Inoue; K Nakanishi
Journal:  Tetrahedron Lett       Date:  1969-03       Impact factor: 2.415

8.  Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation.

Authors:  Katrina H Jensen; Tejas P Pathak; Yang Zhang; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

9.  Palladium-catalyzed direct arylation of (hetero)arenes with aryl boronic acids.

Authors:  Shang-Dong Yang; Chang-Liang Sun; Zhao Fang; Bi-Jie Li; Yi-Zhou Li; Zhang-Jie Shi
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336
  9 in total
  45 in total

1.  A General, Simple Catalyst for Enantiospecific Cross Couplings of Benzylic Ammonium Triflates and Boronic Acids: No Phosphine Ligand Required.

Authors:  Danielle M Shacklady-McAtee; Kelsey M Roberts; Corey H Basch; Ye-Geun Song; Mary P Watson
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

2.  Intercepting Wacker intermediates with arenes: C-H functionalization and dearomatization.

Authors:  Bryan S Matsuura; Allison G Condie; Ian A McBee; Ryan C Buff; Gregory J Karahalis; Corey R J Stephenson
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

3.  Palladium-catalyzed hydrofunctionalization of vinyl phenol derivatives with heteroaromatics.

Authors:  Tejas P Pathak; Matthew S Sigman
Journal:  Org Lett       Date:  2011-04-21       Impact factor: 6.005

4.  Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

Authors:  Yan Miller; Lei Miao; Azade S Hosseini; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2012-07-05       Impact factor: 15.419

5.  Synthesis and Preliminary Biological Study of Bisindolylmethanes Accessed by an Acid-Catalyzed Hydroarylation of Vinylindoles.

Authors:  Tejas P Pathak; Jaroslaw G Osiak; Rachel M Vaden; Bryan E Welm; Matthew S Sigman
Journal:  Tetrahedron       Date:  2012-07-01       Impact factor: 2.457

6.  Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Chem Sci       Date:  2013-07-01       Impact factor: 9.825

7.  Mechanism and enantioselectivity in palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones: insights from computation and experiment.

Authors:  Jeffrey C Holder; Lufeng Zou; Alexander N Marziale; Peng Liu; Yu Lan; Michele Gatti; Kotaro Kikushima; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-09-27       Impact factor: 15.419

8.  Preparation of (S)-tert-ButylPyOx and Palladium-catalyzed Asymmetric Conjugate Addition of Arylboronic Acids.

Authors:  Jeffrey C Holder; Samantha E Shockley; Mario P Wiesenfeldt; Hideki Shimizu; Brian M Stoltz
Journal:  Organic Synth       Date:  2016-03-04

9.  Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols.

Authors:  Nicholas J Race; Cristiane S Schwalm; Takayuki Nakamuro; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-12-01       Impact factor: 15.419

10.  Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes.

Authors:  Qi Zhou; Harathi D Srinivas; Srimoyee Dasgupta; Mary P Watson
Journal:  J Am Chem Soc       Date:  2013-02-20       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.