Literature DB >> 23527796

Biomimetic synthesis of zeylanone and zeylanone epoxide by dimerization of 2-methyl-1,4-naphthoquinone.

Sayako Maruo1, Kazuyuki Nishio, Takahiro Sasamori, Norihiro Tokitoh, Kouji Kuramochi, Kazunori Tsubaki.   

Abstract

A biomimetic synthesis of zeylanone and zeylanone epoxide, which are natural dimeric naphthoquinones, has been accomplished starting from plumbagin, a natural monomeric naphthoquinone. The key features of our synthesis are cascade intermolecular and intramolecular Michael reactions, followed by epoxidation of the resultant hydroquinone with molecular oxygen.

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Year:  2013        PMID： 23527796     DOI： 10.1021/ol400335s

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


  3 in total

1.  Structure, dynamics, and molecular inhibition of the Staphylococcus aureus m1A22-tRNA methyltransferase TrmK.

Authors:  Pamela Sweeney; Ashleigh Galliford; Abhishek Kumar; Dinesh Raju; Naveen B Krishna; Emmajay Sutherland; Caitlin J Leo; Gemma Fisher; Roopa Lalitha; Likith Muthuraj; Gladstone Sigamani; Verena Oehler; Silvia Synowsky; Sally L Shirran; Tracey M Gloster; Clarissa M Czekster; Pravin Kumar; Rafael G da Silva
Journal:  J Biol Chem       Date:  2022-05-17       Impact factor: 5.486

2.  Total Synthesis Establishes the Biosynthetic Pathway to the Naphterpin and Marinone Natural Products.

Authors:  Lauren A M Murray; Shaun M K McKinnie; Henry P Pepper; Reto Erni; Zachary D Miles; Michelle C Cruickshank; Borja López-Pérez; Bradley S Moore; Jonathan H George
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-23       Impact factor: 15.336

3.  Generation of Aryl Radicals from Aryl Hydrazines via Catalytic Iodine in Air: Arylation of Substituted 1,4-Naphthoquinones.

Authors:  Saibal Sar; Jyoti Chauhan; Subhabrata Sen
Journal:  ACS Omega       Date:  2020-02-21
  3 in total

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