Literature DB >> 21488628

Stereoselective synthesis of β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones.

David M Hodgson1, Eric P A Talbot, Barry P Clark.   

Abstract

Zinc or a chromium(II) source with 3-(bromomethyl)furan-2(5H)-one (3) and an aldehyde gives β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones 5 in good yields and high diastereoselectivities. The methodology is demonstrated in concise syntheses of (±)-hydroxymatairesinol (8) and (±)-methylenolactocin (10) by subsequent arylboronate conjugate addition and translactonization, respectively.

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Year:  2011        PMID： 21488628     DOI： 10.1021/ol200711f

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


  5 in total

1.  Targeting NF-κB p65 with a Helenalin Inspired Bis-electrophile.

Authors:  John C Widen; Aaron M Kempema; Peter W Villalta; Daniel A Harki
Journal:  ACS Chem Biol       Date:  2016-11-28       Impact factor: 5.100

2.  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

3.  Divergent synthesis and identification of the cellular targets of deoxyelephantopins.

Authors:  Roman Lagoutte; Christelle Serba; Daniel Abegg; Dominic G Hoch; Alexander Adibekian; Nicolas Winssinger
Journal:  Nat Commun       Date:  2016-08-19       Impact factor: 14.919

4.  From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction-Heck Arylation Sequence.

Authors:  Arbia Talbi; Anne Gaucher; Flavien Bourdreux; Jérôme Marrot; Mohamed L Efrit; Hédi M'Rabet; Damien Prim
Journal:  Molecules       Date:  2017-12-08       Impact factor: 4.411

5.  Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones.

Authors:  Mattia Lazzarotto; Lucas Hammerer; Michael Hetmann; Annika Borg; Luca Schmermund; Lorenz Steiner; Peter Hartmann; Ferdinand Belaj; Wolfgang Kroutil; Karl Gruber; Michael Fuchs
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-08       Impact factor: 15.336
  5 in total

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