Literature DB >> 11871905

Squaric acid ester-based total synthesis of echinochrome A.

Eduardo Peña-Cabrera1, Lanny S Liebeskind.   

Abstract

The total synthesis of echinochrome A is described. Both key intermediates 5 and 8 were efficiently prepared from diisopropyl squarate 7. Nucleophilic addition of aryllithium 8 to 5, followed by thermal ring-expansion/cyclization of the 1,2-adduct 4, furnished hydroquinone 3. Oxidation and full deprotection of 3 gave the title compound.

Entities:  

Mesh:

Substances:

Year:  2002        PMID: 11871905     DOI: 10.1021/jo016034m

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


  5 in total

Review 1.  Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis.

Authors:  Peng-Hao Chen; Guangbin Dong
Journal:  Chemistry       Date:  2016-09-13       Impact factor: 5.236

2.  Pd-catalyzed, Cu(I)-mediated cross-couplings of bisarylthiocyclobutenediones with boronic acids and organostannanes.

Authors:  Angélica Aguilar-Aguilar; Lanny S Liebeskind; Eduardo Peña-Cabrera
Journal:  J Org Chem       Date:  2007-09-25       Impact factor: 4.354

Review 3.  Naphthoquinones of the spinochrome class: occurrence, isolation, biosynthesis and biomedical applications.

Authors:  Yakun Hou; Elena A Vasileva; Alan Carne; Michelle McConnell; Alaa El-Din A Bekhit; Natalia P Mishchenko
Journal:  RSC Adv       Date:  2018-09-21       Impact factor: 4.036

4.  Synthesis of an isotopically labeled naphthalene derivative that supports a long-lived nuclear singlet state.

Authors:  Joseph T Hill-Cousins; Ionut-Alexandru Pop; Giuseppe Pileio; Gabriele Stevanato; Pär Håkansson; Soumya S Roy; Malcolm H Levitt; Lynda J Brown; Richard C D Brown
Journal:  Org Lett       Date:  2015-04-21       Impact factor: 6.005

5.  Amelioration of endotoxin-induced uveitis treated with the sea urchin pigment echinochrome in rats.

Authors:  Anton Lennikov; Nobuyoshi Kitaichi; Kousuke Noda; Kazuomi Mizuuchi; Ryo Ando; Zhenyu Dong; Junichi Fukuhara; Satoshi Kinoshita; Kenichi Namba; Shigeaki Ohno; Susumu Ishida
Journal:  Mol Vis       Date:  2014-02-07       Impact factor: 2.367

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.