Literature DB >> 18582058

ortho-Quinone methides from para-quinones: total synthesis of rubioncolin B.

Jean-Philip Lumb1, Kevin C Choong, Dirk Trauner.   

Abstract

A concise synthesis of rubioncolin B is described, which features an unprecedented intramolecular Diels-Alder reaction involving an ortho-quinone methide and a naphthofuran moiety. The ortho-quinone methide is generated through a surprisingly facile tautomerization of a para-quinone.

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Year:  2008        PMID: 18582058     DOI: 10.1021/ja803498r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  11 in total

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3.  A formal [4 + 4] complementary ambiphile pairing reaction: a new cyclization pathway for ortho-quinone methides.

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4.  Synthesis of novel and diverse naphtho[1,2-b]furans by phosphine-catalyzed [3+2] annulation of activated 1,4-naphthoquinones and acetylenecarboxylates.

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5.  A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A.

Authors:  Alexander J E Novak; Claire E Grigglestone; Dirk Trauner
Journal:  J Am Chem Soc       Date:  2019-09-23       Impact factor: 15.419

6.  Iron-catalyzed rearrangements and cycloaddition reactions of 2H-chromenes.

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7.  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
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8.  Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols.

Authors:  Keith S Barbato; Yi Luan; Daniele Ramella; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2015-11-18       Impact factor: 6.005

9.  Re2O7-catalyzed formal [3 + 2] cycloaddition for diverse naphtho[1,2-b]furan-3-carboxamides and their biological evaluation.

Authors:  Likai Xia; Akber Idhayadhulla; Yong Rok Lee
Journal:  Mol Divers       Date:  2015-08-11       Impact factor: 2.943

10.  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

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