Literature DB >> 18817403

Total syntheses of racemic, natural (-) and unnatural (+) glyceollin I.

Rahul S Khupse1, Paul W Erhardt.   

Abstract

The first total syntheses of racemic glyceollin I and its enantiomers are described. A Wittig approach was utilized as an entry to the appropriately substituted isoflav-3-ene so that an osmium tetroxide mediated asymmetric dihydroxylation could be deployed for stereospecific introduction of the 6a-hydroxy group. While using triphenylphosphine hydrobromide, a novel method was found for gently removing MOM from protected phenolic hydroxyl groups present within sensitive systems.

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Year:  2008        PMID: 18817403     DOI: 10.1021/ol802112r

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


  4 in total

1.  Effects of 7-O substitutions on estrogenic and anti-estrogenic activities of daidzein analogues in MCF-7 breast cancer cells.

Authors:  Quan Jiang; Florastina Payton-Stewart; Steven Elliott; Jennifer Driver; Lyndsay V Rhodes; Qiang Zhang; Shilong Zheng; Deepak Bhatnagar; Stephen M Boue; Bridgette M Collins-Burow; Jayalakshmi Sridhar; Cheryl Stevens; John A McLachlan; Thomas E Wiese; Matthew E Burow; Guangdi Wang
Journal:  J Med Chem       Date:  2010-08-26       Impact factor: 7.446

2.  Glyceollins trigger anti-proliferative effects through estradiol-dependent and independent pathways in breast cancer cells.

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Journal:  Cell Commun Signal       Date:  2017-06-30       Impact factor: 5.712

3.  Asymmetric one-pot transformation of isoflavones to pterocarpans and its application in phytoalexin synthesis.

Authors:  Philipp Ciesielski; Peter Metz
Journal:  Nat Commun       Date:  2020-06-18       Impact factor: 14.919

Review 4.  Recent Advances in the Application of Selectfluor™ F-TEDA-BF4 as a Versatile Mediator or Catalyst in Organic Synthesis.

Authors:  Stojan Stavber
Journal:  Molecules       Date:  2011-07-29       Impact factor: 4.411

  4 in total

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