Literature DB >> 29993045

Recent advances in the application of Diels-Alder reactions involving o-quinodimethanes, aza-o-quinone methides and o-quinone methides in natural product total synthesis.

Baochao Yang1, Shuanhu Gao.   

Abstract

In recent decades, transient and highly reactive ortho-quinodimethanes (o-QDMs), ortho-quinone methides (o-QMs) and aza-ortho-quinone methides (aza-o-QMs) have attracted much attention and have been extensively studied and applied in organic synthesis, especially natural product total synthesis. This review summarizes recent advances in Diels-Alder reactions involving in situ-generated o-QDMs, o-QMs and aza-o-QMs, highlighting the power and potential of this strategy in organic synthesis and natural product total synthesis. An overview of the methods for generating these intermediates is also available.

Entities:  

Year:  2018        PMID: 29993045     DOI: 10.1039/c8cs00274f

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  25 in total

1.  Chemoenzymatic o-Quinone Methide Formation.

Authors:  Tyler J Doyon; Jonathan C Perkins; Summer A Baker Dockrey; Evan O Romero; Kevin C Skinner; Paul M Zimmerman; Alison R H Narayan
Journal:  J Am Chem Soc       Date:  2019-12-16       Impact factor: 15.419

2.  Carbene-Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones.

Authors:  Ansoo Lee; Joshua L Zhu; Taisiia Feoktistova; Alexander C Brueckner; Paul H-Y Cheong; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-27       Impact factor: 15.336

3.  Selective radical cascade (4+2) annulation with olefins towards the synthesis of chroman derivatives via organo-photoredox catalysis.

Authors:  Zhipeng Guan; Xingxing Zhong; Yayu Ye; Xiangwei Li; Hengjiang Cong; Hong Yi; Heng Zhang; Zhiliang Huang; Aiwen Lei
Journal:  Chem Sci       Date:  2022-04-21       Impact factor: 9.969

4.  Palladium-Catalyzed Access to Benzocyclobutenone-Derived Ketonitrones via C(sp2)-H Functionalization.

Authors:  Jakub Brześkiewicz; Rafał Loska
Journal:  Org Lett       Date:  2022-05-25       Impact factor: 6.072

5.  Chemoselective oxidative generation of ortho-quinone methides and tandem transformations.

Authors:  Muhammet Uyanik; Kohei Nishioka; Ryutaro Kondo; Kazuaki Ishihara
Journal:  Nat Chem       Date:  2020-03-23       Impact factor: 24.427

6.  A formal intermolecular [4 + 1] cycloaddition reaction of 3-chlorooxindole and o-quinone methides: a facile synthesis of spirocyclic oxindole scaffolds.

Authors:  Chao Lin; Qi Xing; Honglei Xie
Journal:  RSC Adv       Date:  2021-05-24       Impact factor: 4.036

Review 7.  Light-Triggered Click Chemistry.

Authors:  Gangam Srikanth Kumar; Qing Lin
Journal:  Chem Rev       Date:  2020-10-26       Impact factor: 72.087

Review 8.  Harnessing ortho-Quinone Methides in Natural Product Biosynthesis and Biocatalysis.

Authors:  Trevor N Purdy; Bradley S Moore; April L Lukowski
Journal:  J Nat Prod       Date:  2022-02-02       Impact factor: 4.803

9.  Wearable piezoelectric mass sensor based on pH sensitive hydrogels for sweat pH monitoring.

Authors:  E Scarpa; V M Mastronardi; F Guido; L Algieri; A Qualtieri; R Fiammengo; F Rizzi; M De Vittorio
Journal:  Sci Rep       Date:  2020-07-02       Impact factor: 4.379

10.  Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels-Alder Reactions of Cyclohexadienones with Cyclopentadiene.

Authors:  Santanu Ghosh; Sayantani Das; Chandra Kanta De; Diana Yepes; Frank Neese; Giovanni Bistoni; Markus Leutzsch; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-11       Impact factor: 15.336

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