Literature DB >> 21942286

Microwave-based reaction screening: tandem retro-Diels-Alder/Diels-Alder cycloadditions of o-quinol dimers.

Suwei Dong1, Katharine J Cahill, Moon-Il Kang, Nancy H Colburn, Curtis J Henrich, Jennifer A Wilson, John A Beutler, Richard P Johnson, John A Porco.   

Abstract

We have accomplished a parallel screen of cycloaddition partners for o-quinols utilizing a plate-based microwave system. Microwave irradiation improves the efficiency of retro-Diels-Alder/Diels-Alder cascades of o-quinol dimers which generally proceed in a diastereoselective fashion. Computational studies indicate that asynchronous transition states are favored in Diels-Alder cycloadditions of o-quinols. Subsequent biological evaluation of a collection of cycloadducts has identified an inhibitor of activator protein-1 (AP-1), an oncogenic transcription factor.

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Year:  2011        PMID： 21942286      PMCID： PMC3214659          DOI： 10.1021/jo201658y

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


  30 in total

1.  Cyclohexadienone ketals and quinols: four building blocks potentially useful for enantioselective synthesis.

Authors:  D Magdziak; S J Meek; T R R Pettus
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

2.  Domino retro Diels-Alder/Diels-Alder reaction: an efficient protocol for the synthesis of highly functionalized bicyclo[2.2.2]octenones and bicyclo[2.2.2]octadienones.

Authors:  Santhosh Kumar Chittimalla; Hui-Yi Shiao; Chun-Chen Liao
Journal:  Org Biomol Chem       Date:  2006-05-04       Impact factor: 3.876

3.  Investigating the existence of nonthermal/specific microwave effects using silicon carbide heating elements as power modulators.

Authors:  Tahseen Razzaq; Jennifer M Kremsner; C Oliver Kappe
Journal:  J Org Chem       Date:  2008-07-10       Impact factor: 4.354

4.  High-throughput experimentation platform: parallel microwave chemistry in HPLC/GC vials.

Authors:  Markus Damm; C Oliver Kappe
Journal:  J Comb Chem       Date:  2009 May-Jun

5.  A high-throughput cell-based assay to identify specific inhibitors of transcription factor AP-1.

Authors:  Katie M Ruocco; Ekaterina I Goncharova; Matthew R Young; Nancy H Colburn; James B McMahon; Curtis J Henrich
Journal:  J Biomol Screen       Date:  2006-12-14

6.  Parallel microwave chemistry in silicon carbide reactor platforms: an in-depth investigation into heating characteristics.

Authors:  Markus Damm; C Oliver Kappe
Journal:  Mol Divers       Date:  2009-06-23       Impact factor: 2.943

7.  Microwave dielectric heating in synthetic organic chemistry.

Authors:  C Oliver Kappe
Journal:  Chem Soc Rev       Date:  2008-04-21       Impact factor: 54.564

8.  Total synthesis of the quinone epoxide dimer (+)-torreyanic acid: application of a biomimetic oxidation/electrocyclization/Diels-Alder dimerization cascade.

Authors:  Chaomin Li; Richard P Johnson; John A Porco
Journal:  J Am Chem Soc       Date:  2003-04-30       Impact factor: 15.419

9.  Silicon carbide passive heating elements in microwave-assisted organic synthesis.

Authors:  Jennifer M Kremsner; C Oliver Kappe
Journal:  J Org Chem       Date:  2006-06-09       Impact factor: 4.354

10.  Rhodium-catalyzed methylenation of aldehydes.

Authors:  Hélène Lebel; Valérie Paquet
Journal:  J Am Chem Soc       Date:  2004-01-14       Impact factor: 15.419
View more
  8 in total

Review 1.  Parallel microwave chemistry in silicon carbide microtiter platforms: a review.

Authors:  C Oliver Kappe; Markus Damm
Journal:  Mol Divers       Date:  2011-11-30       Impact factor: 2.943

2.  Synthesis of chamaecypanone C analogues from in situ-generated cyclopentadienones and their biological evaluation.

Authors:  Suwei Dong; Tian Qin; Ernest Hamel; John A Beutler; John A Porco
Journal:  J Am Chem Soc       Date:  2012-11-20       Impact factor: 15.419

3.  High-throughput Screening in Larval Zebrafish Identifies Novel Potent Sedative-hypnotics.

Authors:  Xiaoxuan Yang; Youssef Jounaidi; Jennifer B Dai; Francisco Marte-Oquendo; Elizabeth S Halpin; Lauren E Brown; Richard Trilles; Wenqing Xu; Renee Daigle; Buwei Yu; Scott E Schaus; John A Porco; Stuart A Forman
Journal:  Anesthesiology       Date:  2018-09       Impact factor: 7.892

4.  High-speed C-H chlorination of ethylene carbonate using a new photoflow setup.

Authors:  Takayoshi Kasakado; Tomohiro Nakagawa; Shinji Taguchi; Takahide Fukuyama; Ilhyong Ryu
Journal:  Beilstein J Org Chem       Date:  2022-01-27       Impact factor: 2.883

5.  Organocatalytic Enantioselective Synthesis of Bicyclo[2.2.2]octenones via Oxaziridinium Catalysed ortho-Hydroxylative Phenol Dearomatization.

Authors:  Tom D D'Arcy; Mark R J Elsegood; Benjamin R Buckley
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-10       Impact factor: 16.823

6.  A facile and efficient synthesis of diaryl amines or ethers under microwave irradiation at presence of KF/Al2O3 without solvent and their anti-fungal biological activities against six phytopathogens.

Authors:  Liang-Zhu Huang; Pan Han; You-Qiang Li; Ying-Meng Xu; Tao Zhang; Zhen-Ting Du
Journal:  Int J Mol Sci       Date:  2013-09-12       Impact factor: 5.923

7.  Multidimensional reaction screening for photochemical transformations as a tool for discovering new chemotypes.

Authors:  Véronique I Martin; John R Goodell; Oscar J Ingham; John A Porco; Aaron B Beeler
Journal:  J Org Chem       Date:  2014-04-16       Impact factor: 4.354

8.  Small molecule inhibitors targeting activator protein 1 (AP-1).

Authors:  Na Ye; Ye Ding; Christopher Wild; Qiang Shen; Jia Zhou
Journal:  J Med Chem       Date:  2014-05-27       Impact factor: 8.039
  8 in total

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