Literature DB >> 15101738

Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products.

Joshua Fischer1, Aaron J Reynolds, Lisa A Sharp, Michael S Sherburn.   

Abstract

[reaction: see text] Total syntheses of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)-alpha-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be erroneous; a diastereoisomeric structure is assigned to the natural product.

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Year:  2004        PMID： 15101738     DOI： 10.1021/ol049878b

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


  8 in total

1.  Facile Preparation of Spirolactones by an Alkoxycarbonyl Radical Cyclization-Cross-Coupling Cascade.

Authors:  Nicholas A Weires; Yuriy Slutskyy; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-13       Impact factor: 15.336

Review 2.  Recent strategies and tactics for the enantioselective total syntheses of cyclolignan natural products.

Authors:  Rebekah G Reynolds; Huong Quynh Anh Nguyen; Jordan C T Reddel; Regan J Thomson
Journal:  Nat Prod Rep       Date:  2022-03-23       Impact factor: 13.423

Review 3.  Lignans as Pharmacological Agents in Disorders Related to Oxidative Stress and Inflammation: Chemical Synthesis Approaches and Biological Activities.

Authors:  Dmitry I Osmakov; Aleksandr P Kalinovskii; Olga A Belozerova; Yaroslav A Andreev; Sergey A Kozlov
Journal:  Int J Mol Sci       Date:  2022-05-27       Impact factor: 6.208

4.  Lignans from Carthamus tinctorius suppress tryptophan breakdown via indoleamine 2,3-dioxygenase.

Authors:  Susanne Kuehnl; Sebastian Schroecksnadel; Veronika Temml; Johanna M Gostner; Harald Schennach; Daniela Schuster; Stefan Schwaiger; Judith M Rollinger; Dietmar Fuchs; Hermann Stuppner
Journal:  Phytomedicine       Date:  2013-07-15       Impact factor: 5.340

5.  Asymmetric Synthesis of β-Substituted α-Methylenebutyro- lactones via TRIP-Catalyzed Allylation: Mechanistic Studies and Application to the Synthesis of (S)-(-)-Hydroxymatairesinol.

Authors:  Michael Fuchs; Markus Schober; Andreas Orthaber; Kurt Faber
Journal:  Adv Synth Catal       Date:  2013-08-29       Impact factor: 5.837

Review 6.  Recent applications of the (TMS)3SiH radical-based reagent.

Authors:  Chryssostomos Chatgilialoglu; Jacques Lalevée
Journal:  Molecules       Date:  2012-01-06       Impact factor: 4.411

7.  Untargeted liquid chromatography coupled with mass spectrometry reveals metabolic changes in nitrogen-deficient Isatis indigotica Fortune.

Authors:  Yi-Wen Cao; Ren-Jun Qu; Yu-Jing Miao; Xiao-Qing Tang; Ying Zhou; Lei Wang; Li Geng
Journal:  Phytochemistry       Date:  2019-07-04       Impact factor: 4.072

8.  Arctigenin: pharmacology, total synthesis, and progress in structure modification.

Authors:  Dan Wu; Lili Jin; Xing Huang; Hao Deng; Qing-Kun Shen; Zhe-Shan Quan; Changhao Zhang; Hong-Yan Guo
Journal:  J Enzyme Inhib Med Chem       Date:  2022-12       Impact factor: 5.756
  8 in total

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