Literature DB >> 26726272

First ketene cycloaddition approach to (±)-junionone.

Ihsan Erden1, Samuel E Watson1.   

Abstract

Junionone is the first monocyclic cyclobutane monoterpenoid isolated from a plant. Of the existing four syntheses of this compound, none employs a ketene cycloaddition to construct the four-membered ring. Herein, we report the first total synthesis of junionone that features a ketene cycloaddition for the synthesis of this compound, starting from the commercially available 1,5-hexadiene. 2009 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Huang-Minlon reduction; Wacker-Tsuji oxidation; cyclobutanone; dimethylketene; junionone

Year:  2016        PMID： 26726272      PMCID： PMC4695394          DOI： 10.1016/j.tetlet.2015.12.043

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  5 in total

1.  Recent advancements and challenges of palladium(II)-catalyzed oxidation reactions with molecular oxygen as the sole oxidant.

Authors:  Keith M Gligorich; Matthew S Sigman
Journal:  Chem Commun (Camb)       Date:  2009-05-14       Impact factor: 6.222

2.  A three-carbon (n+1+2) ring expansion method for the synthesis of macrocyclic enones. Application to muscone synthesis.

Authors:  Ihsan Erden; Weiguo Cao; Mary Price; Michael Colton
Journal:  Tetrahedron       Date:  2008-06-02       Impact factor: 2.457

3.  Total synthesis of junionone, a natural monoterpenoid from Juniperus communis L., and determination of the absolute configuration of the naturally occurring enantiomer by ROA spectroscopy.

Authors:  Martin A Lovchik; Georg Fráter; Andreas Goeke; Werner Hug
Journal:  Chem Biodivers       Date:  2008-01       Impact factor: 2.408

4.  Sex pheromone of the citrus mealybug Planococcus citri: synthesis and optimization of trap parameters.

Authors:  A Zada; E Dunkelblum; M Harel; F Assael; S Gross; Z Mendel
Journal:  J Econ Entomol       Date:  2004-04       Impact factor: 2.381

5.  Sex pheromones produced by male boll weevil: isolation, identification, and synthesis.

Authors:  J H Tumlinson; D D Hardee; R C Gueldner; A C Thompson; P A Hedin; J P Minyard
Journal:  Science       Date:  1969-11-21       Impact factor: 47.728
  5 in total
  1 in total

Review 1.  Recent advances in the synthesis of gem-dimethylcyclobutane natural products.

Authors:  Erin N Hancock; Johannes M Wiest; M Kevin Brown
Journal:  Nat Prod Rep       Date:  2019-10-16       Impact factor: 13.423
  1 in total

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