Literature DB >> 18549215

Vinyl quinones as Diels-Alder dienes: concise synthesis of (-)-halenaquinone.

Michael A Kienzler1, Sandy Suseno, Dirk Trauner.   

Abstract

A concise asymmetric synthesis of (-)-halenaquinone is described. The synthesis features a diastereoselective Heck cyclization to set a quaternary center as well as a novel intramolecular inverse-electron-demand Diels-Alder reaction involving a vinyl quinone. The synthesis is highly convergent and features a minimal amount of protecting group manipulations.

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Year:  2008        PMID： 18549215     DOI： 10.1021/ja8035042

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


  4 in total

1.  Strategies for the Synthesis of the Halenaquinol and Xestoquinol Families of Natural Products.

Authors:  Gregg M Schwarzwalder; Christopher D Vanderwal
Journal:  European J Org Chem       Date:  2017-02-16

Review 2.  Synthetic strategies to terpene quinones/hydroquinones.

Authors:  Marina Gordaliza
Journal:  Mar Drugs       Date:  2012-02-14       Impact factor: 6.085

3.  Copper-catalyzed cascade annulation of unsaturated α-bromocarbonyls with enynals: a facile access to ketones from aldehydes.

Authors:  Chao Che; Qianwen Huang; Hanliang Zheng; Gangguo Zhu
Journal:  Chem Sci       Date:  2016-03-04       Impact factor: 9.825

Review 4.  Assessment on facile Diels-Alder approach of α-pyrone and terpenoquinone for the expedient synthesis of various natural scaffolds.

Authors:  Aluru Rammohan; Albert F Khasanov; Dmitry S Kopchuk; Duvvuru Gunasekar; Grigory V Zyryanov; Oleg N Chupakhin
Journal:  Nat Prod Bioprospect       Date:  2022-03-31
  4 in total

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