Literature DB >> 22233235

Mild and rapid method for the generation of ortho-(naphtho)quinone methide intermediates.

Abdul kadar Shaikh1, Alexander J A Cobb, George Varvounis.   

Abstract

A new mild method has been devised for generating o-(naphtho)quinone methides via fluoride-induced desilylation of silyl derivatives of o-hydroxybenzyl(or 1-naphthylmethyl) nitrate. The reactive o-(naphtho)quinone methide intermediates were trapped by C, O, N, and S nucleophiles and underwent "inverse electron-demand" hetero-Diels-Alder reaction with dienophiles to give stable adducts. The method has useful potential application in natural product synthesis and drug research.
© 2012 American Chemical Society

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Year:  2012        PMID： 22233235     DOI： 10.1021/ol203196n

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


  5 in total

1.  Michael Additions of Highly Basic Enolates to ortho-Quinone Methides.

Authors:  Robert S Lewis; Christopher J Garza; Ann T Dang; Te Kie A Pedro; William J Chain
Journal:  Org Lett       Date:  2015-04-23       Impact factor: 6.005

2.  Study of para-Quinone Methide Precursors toward the Realkylation of Aged Acetylcholinesterase.

Authors:  Ryan J Yoder; Qinggeng Zhuang; Jeremy M Beck; Andrew Franjesevic; Travis G Blanton; Sydney Sillart; Tyler Secor; Leah Guerra; Jason D Brown; Carolyn Reid; Craig A McElroy; Özlem Doğan Ekici; Christopher S Callam; Christopher M Hadad
Journal:  ACS Med Chem Lett       Date:  2017-05-08       Impact factor: 4.345

3.  Antineoplastic Isoflavonoids Derived from Intermediate ortho-Quinone Methides Generated from Mannich Bases.

Authors:  Mykhaylo S Frasinyuk; Galyna P Mrug; Svitlana P Bondarenko; Volodymyr P Khilya; Vitaliy M Sviripa; Oleksandr A Syrotchuk; Wen Zhang; Xianfeng Cai; Michael V Fiandalo; James L Mohler; Chunming Liu; David S Watt
Journal:  ChemMedChem       Date:  2016-02-17       Impact factor: 3.466

4.  The domestication of ortho-quinone methides.

Authors:  Wen-Ju Bai; Jonathan G David; Zhen-Gao Feng; Marisa G Weaver; Kun-Liang Wu; Thomas R R Pettus
Journal:  Acc Chem Res       Date:  2014-12-03       Impact factor: 22.384

5.  Redox-neutral α-oxygenation of amines: reaction development and elucidation of the mechanism.

Authors:  Matthew T Richers; Martin Breugst; Alena Yu Platonova; Anja Ullrich; Arne Dieckmann; K N Houk; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2014-04-14       Impact factor: 15.419
  5 in total

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