Literature DB >> 19860387

A one-pot, base-free annelation approach to alpha-alkylidene-gamma-butyrolactones.

Russell R A Kitson1, Richard J K Taylor, John L Wood.   

Abstract

A novel annelation procedure has been developed for the conversion of gamma-hydoxy enones into alpha-alkylidene-gamma-butyrolactones. This one-pot method utilizes the Bestmann ylide (triphenylphosphoranylideneketene) and proceeds by way of acylation followed by an intramolecular conjugate addition/proton transfer/Wittig olefination sequence. The procedure is "base-free" and is useful for the preparation of a range of alpha-alkylidene-gamma-butyrolactones including alpha-methylene-gamma-butyrolactone examples, which can be particularly base-sensitive.

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Year:  2009        PMID： 19860387     DOI： 10.1021/ol902191d

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


  3 in total

1.  Total Synthesis of (±)-Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen-Oxygen Bonds.

Authors:  Kyle M Lambert; Joshua B Cox; Lin Liu; Amy C Jackson; Sam Yruegas; Kenneth B Wiberg; John L Wood
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-08       Impact factor: 15.336

2.  Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: Synthesis of a new class of spirocyclic ketal-lactones.

Authors:  Alberto Munoz; Ryan P Murelli
Journal:  Tetrahedron Lett       Date:  2012-10-12       Impact factor: 2.415

3.  Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach.

Authors:  Jingjing Wang; Samuel Z Y Ting; Joanne E Harvey
Journal:  Beilstein J Org Chem       Date:  2015-10-05       Impact factor: 2.883
  3 in total

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