Literature DB >> 28426216

Total Syntheses of Highly Oxidized ent-Kaurenoids Pharicin A, Pharicinin B, 7-O-Acetylpseurata C, and Pseurata C: A [5+2] Cascade Approach.

Chi He1, Jialei Hu1, Yubing Wu1, Hanfeng Ding1,2.   

Abstract

The unprecedented oxidative dearomatization-induced [5+2] cycloaddition/pinacol-type 1,2-acyl migration cascade efficiently generates a quaternary carbon center and assembles the highly oxygenated bicyclo[3.2.1]octane framework of ent-kaurene diterpenoids. By incorporation of the subsequent retro-aldol/aldol process and singlet oxygen ene reaction, this concise and convergent approach has enabled the first asymmetric total syntheses of pharicin A, pharicinin B, 7-O-acetylpseurata C, and pseurata C.

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Year:  2017        PMID: 28426216     DOI: 10.1021/jacs.7b02746

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


  6 in total

1.  Shaping Molecular Landscapes: Recent Advances, Opportunities, and Challenges in Dearomatization.

Authors:  Christopher J Huck; David Sarlah
Journal:  Chem       Date:  2020-07-01       Impact factor: 22.804

Review 2.  Transition Metal-Mediated C-C Single Bond Cleavage: Making the Cut in Total Synthesis.

Authors:  Brian Wang; Melecio A Perea; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-24       Impact factor: 15.336

3.  Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid.

Authors:  Aneta Turlik; Yifeng Chen; Anthony C Scruse; Timothy R Newhouse
Journal:  J Am Chem Soc       Date:  2019-05-07       Impact factor: 15.419

4.  Scalable synthesis enabling multilevel bio-evaluations of natural products for discovery of lead compounds.

Authors:  Lizhi Zhu; Wenjing Ma; Mengxun Zhang; Magnolia Muk-Lan Lee; Wing-Yan Wong; Brandon Dow Chan; Qianqian Yang; Wing-Tak Wong; William Chi-Shing Tai; Chi-Sing Lee
Journal:  Nat Commun       Date:  2018-03-29       Impact factor: 14.919

5.  Constructing chiral bicyclo[3.2.1]octanes via palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes.

Authors:  Zhenbo Yuan; Yuye Zeng; Ziwen Feng; Zhe Guan; Aijun Lin; Hequan Yao
Journal:  Nat Commun       Date:  2020-05-21       Impact factor: 14.919

6.  Unexpected Racemization in the Course of the Acetalization of (+)-(S)-5-Methyl-Wieland-Miescher Ketone with 1,2-Ethanediol and TsOH under Classical Experimental Conditions.

Authors:  Francesca Leonelli; Irene Piergentili; Giulio Lucarelli; Luisa Maria Migneco; Rinaldo Marini Bettolo
Journal:  Int J Mol Sci       Date:  2019-12-05       Impact factor: 5.923

  6 in total

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