Literature DB >> 26735066

Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products Sanggenons C and O.

Chao Qi1, Yuan Xiong1, Vincent Eschenbrenner-Lux1, Huan Cong1, John A Porco1.   

Abstract

Metal-catalyzed, double Claisen rearrangement of a bis-allyloxyflavone has been utilized to enable a concise synthesis of the hydrobenzofuro[3,2-b]chromenone core structure of the natural products sanggenon A and sanggenol F. In addition, catalytic, enantioselective [4+2] cycloadditions of 2'-hydroxychalcones have been accomplished using B(OPh)3/BINOL complexes. Asymmetric syntheses of the flavonoid Diels-Alder natural products sanggenons C and O have been achieved employing a stereodivergent reaction of a racemic mixture (stereodivergent RRM) involving [4+2] cycloaddition.

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Year:  2016        PMID： 26735066      PMCID： PMC4863937          DOI： 10.1021/jacs.5b12778

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


  27 in total

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6.  Molecular complexity via C-H activation: a dehydrogenative Diels-Alder reaction.

Authors:  Erik M Stang; M Christina White
Journal:  J Am Chem Soc       Date:  2011-09-01       Impact factor: 15.419

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8.  Biomimetic dehydrogenative Diels-Alder cycloadditions: total syntheses of brosimones A and B.

Authors:  Chao Qi; Huan Cong; Katharine J Cahill; Peter Müller; Richard P Johnson; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-01       Impact factor: 15.336

9.  Synthesis of chamaecypanone C analogues from in situ-generated cyclopentadienones and their biological evaluation.

Authors:  Suwei Dong; Tian Qin; Ernest Hamel; John A Beutler; John A Porco
Journal:  J Am Chem Soc       Date:  2012-11-20       Impact factor: 15.419

10.  Enantioselective total synthesis of (-)-napyradiomycin A1 via asymmetric chlorination of an isolated olefin.

Authors:  Scott A Snyder; Zhen-Yu Tang; Ritu Gupta
Journal:  J Am Chem Soc       Date:  2009-04-29       Impact factor: 15.419
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  2 in total

1.  Biomimetic Total Synthesis of (±)-Griffipavixanthone via a Cationic Cycloaddition-Cyclization Cascade.

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Journal:  J Am Chem Soc       Date:  2017-10-02       Impact factor: 15.419

Review 2.  Mulberry Diels-Alder-type adducts: isolation, structure, bioactivity, and synthesis.

Authors:  Si-Yuan Luo; Jun-Yu Zhu; Ming-Feng Zou; Sheng Yin; Gui-Hua Tang
Journal:  Nat Prod Bioprospect       Date:  2022-09-02
  2 in total

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