Literature DB >> 19769386

Approach to tetrodotoxin via the oxidative amidation of a phenol.

Brian A Mendelsohn1, Marco A Ciufolini.   

Abstract

An approach to tetrodotoxin that relies on the oxidative amidation of methyl 4-hydroxyphenylacetate as a key step is described. The stereoselective introduction of a beta-hydroxynitrile functionality on one of the double bonds of the emerging dienone is achieved through an intramolecular nitrile oxide cycloaddition-fragmentation sequence.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19769386     DOI： 10.1021/ol901914u

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


  3 in total

Review 1.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

2.  Highly Functionalized Tricyclic Oxazinanones via Pairwise Oxidative Dearomatization and N-Hydroxycarbamate Dehydrogenation: Molecular Diversity Inspired by Tetrodotoxin.

Authors:  Steffen N Good; Robert J Sharpe; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2017-08-30       Impact factor: 15.419

Review 3.  The chemical synthesis of tetrodoxin: an ongoing quest.

Authors:  Jaclyn Chau; Marco A Ciufolini
Journal:  Mar Drugs       Date:  2011-10-20       Impact factor: 6.085
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.