Literature DB >> 20590087

Biomimetic synthesis of polycyclic polyprenylated acylphloroglucinol natural products isolated from Hypericum papuanum.

Jonathan H George1, Micha D Hesse, Jack E Baldwin, Robert M Adlington.   

Abstract

Biomimetic syntheses of three polycylic polyprenylated acylphloroglucinol natural products isolated from Hypericum papuanum, ialibinone A, ialibinone B, and hyperguinone B, have been accomplished by selective oxidative cyclizations of the proposed biosynthetic precursor 5, which was synthesized from phloroglucinol in three steps.

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Year:  2010        PMID： 20590087     DOI： 10.1021/ol101380a

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


  10 in total

1.  Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.

Authors:  Mikayo Hayashi; Lauren E Brown; John A Porco
Journal:  European J Org Chem       Date:  2016-10

2.  A heteromeric membrane-bound prenyltransferase complex from hop catalyzes three sequential aromatic prenylations in the bitter acid pathway.

Authors:  Haoxun Li; Zhaonan Ban; Hao Qin; Liya Ma; Andrew J King; Guodong Wang
Journal:  Plant Physiol       Date:  2015-01-06       Impact factor: 8.340

3.  Total Synthesis and Anticancer Activity of (+)-Hypercalin C and Congeners.

Authors:  Yongfeng Tao; Keighley Reisenauer; Joseph H Taube; Daniel Romo
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-01       Impact factor: 15.336

4.  Synthetic Efforts Toward [3.3.1] Bridged Bicyclic Phloroglucinol Natural Products.

Authors:  Jon T Njardarson
Journal:  Tetrahedron       Date:  2011-10-07       Impact factor: 2.457

5.  Programmable meroterpene synthesis.

Authors:  Xingyu Shen; Chi P Ting; Gong Xu; Thomas J Maimone
Journal:  Nat Commun       Date:  2020-01-24       Impact factor: 14.919

6.  Bioinspired Total Synthesis of Erectones A and B, and the Revised Structure of Hyperelodione D.

Authors:  Liam J Franov; Jacob D Hart; Glenn A Pullella; Christopher J Sumby; Jonathan H George
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-14       Impact factor: 16.823

7.  Intramolecular Tricarbonyl-Ene Reactions and α-Hydroxy-β-Diketone Rearrangements Inspired by the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols.

Authors:  Andreas B Zur Bonsen; Ricardo A Peralta; Thomas Fallon; David M Huang; Jonathan H George
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-14       Impact factor: 16.823

8.  Synthesis and Multiplexed Activity Profiling of Synthetic Acylphloroglucinol Scaffolds.

Authors:  Jonathan H Boyce; Benjamin J Reisman; Brian O Bachmann; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-30       Impact factor: 15.336

9.  Noncatalytic chalcone isomerase-fold proteins in Humulus lupulus are auxiliary components in prenylated flavonoid biosynthesis.

Authors:  Zhaonan Ban; Hao Qin; Andrew J Mitchell; Baoxiu Liu; Fengxia Zhang; Jing-Ke Weng; Richard A Dixon; Guodong Wang
Journal:  Proc Natl Acad Sci U S A       Date:  2018-05-14       Impact factor: 11.205

10.  Expedient Synthesis of Lupulones and Their Derivatization to 2,8-7H-Dihydrochromen-7-ones.

Authors:  Lena Decuyper; Gurkirat Kaur; Charlotte Versyck; Eline Blondeel; Yves Depetter; Kristof Van Hecke; Matthias D'hooghe
Journal:  ChemistryOpen       Date:  2020-04-06       Impact factor: 2.911
  10 in total

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