Literature DB >> 20387852

Mild arming and derivatization of natural products via an In(OTf)3-catalyzed arene iodination.

Cong-Ying Zhou1, Jing Li, Satyamaheshwar Peddibhotla, Daniel Romo.   

Abstract

Iodination of arene-containing natural products employing N-iodosuccinimide catalyzed by In(OTf)(3) at ambient temperature is reported as a versatile and mild method for natural product derivatization amenable to small scale. This process facilitates natural product derivatization of arene moieties for SAR studies, homo- and heterodimerization of natural products, and also conjugation with reporters such as biotin via subsequent metal-mediated coupling reactions.

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Year:  2010        PMID： 20387852     DOI： 10.1021/ol100587j

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


  22 in total

1.  Cyclopropanations of olefin-containing natural products for simultaneous arming and structure activity studies.

Authors:  Omar Robles; Sergio O Serna-Saldívar; Janet A Gutiérrez-Uribe; Daniel Romo
Journal:  Org Lett       Date:  2012-02-24       Impact factor: 6.005

2.  An alternative to the Sandmeyer approach to aryl iodides.

Authors:  Bao Hu; William H Miller; Kiel D Neumann; Ethan J Linstad; Stephen G DiMagno
Journal:  Chemistry       Date:  2015-03-10       Impact factor: 5.236

3.  Magnesiate Addition/Ring-Expansion Strategy To Access the 6-7-6 Tricyclic Core of Hetisine-Type C20-Diterpenoid Alkaloids.

Authors:  Jason J Pflueger; Louis C Morrill; Justine N deGruyter; Melecio A Perea; Richmond Sarpong
Journal:  Org Lett       Date:  2017-08-18       Impact factor: 6.005

4.  Silanol: a traceless directing group for Pd-catalyzed o-alkenylation of phenols.

Authors:  Chunhui Huang; Buddhadeb Chattopadhyay; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2011-07-21       Impact factor: 15.419

5.  Bioconjugation by native chemical tagging of C-H bonds.

Authors:  Qianghui Zhou; Jinghan Gui; Chung-Mao Pan; Earl Albone; Xin Cheng; Edward M Suh; Luigi Grasso; Yoshihiro Ishihara; Phil S Baran
Journal:  J Am Chem Soc       Date:  2013-08-22       Impact factor: 15.419

6.  Oxidation of organotrifluoroborates via oxone.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2010-12-30       Impact factor: 4.354

Review 7.  Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Authors:  Christopher R Shugrue; Scott J Miller
Journal:  Chem Rev       Date:  2017-06-05       Impact factor: 60.622

8.  Derivatization of agelastatin A leading to bioactive analogs and a trifunctional probe.

Authors:  Morgan Jouanneau; Brandon McClary; Jeremy Chris P Reyes; Rong Chen; Yuling Chen; William Plunkett; Xin Cheng; Andrew Z Milinichik; Earl F Albone; Jun O Liu; Daniel Romo
Journal:  Bioorg Med Chem Lett       Date:  2016-02-23       Impact factor: 2.823

Review 9.  Chemo- and site-selective derivatizations of natural products enabling biological studies.

Authors:  Omar Robles; Daniel Romo
Journal:  Nat Prod Rep       Date:  2014-03       Impact factor: 13.423

10.  Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate.

Authors:  Jing Li; Justin S Cisar; Cong-Ying Zhou; Brunilda Vera; Howard Williams; Abimael D Rodríguez; Benjamin F Cravatt; Daniel Romo
Journal:  Nat Chem       Date:  2013-05-19       Impact factor: 24.427
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