Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone

The commercially available monoterpene carvone has been efficiently convertedinto the tricyclo[3.2.1.02.7]octane and bicyclo[3.2.1]octane systems characteristic of somebiologically active compounds. The sequence used for this transformation involves as keyfeatures an intramolecular Diels-Alder react...

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Main Authors: Noelia Vera, Ismael Navarro, Ignacio de Alfonso, Ana C. Cuñat, Consuelo Agulló, Antonio Abad
Format: Article
Language:English
Published: MDPI AG 2004-04-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/9/5/287/
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author Noelia Vera
Ismael Navarro
Ignacio de Alfonso
Ana C. Cuñat
Consuelo Agulló
Antonio Abad
author_facet Noelia Vera
Ismael Navarro
Ignacio de Alfonso
Ana C. Cuñat
Consuelo Agulló
Antonio Abad
author_sort Noelia Vera
collection DOAJ
description The commercially available monoterpene carvone has been efficiently convertedinto the tricyclo[3.2.1.02.7]octane and bicyclo[3.2.1]octane systems characteristic of somebiologically active compounds. The sequence used for this transformation involves as keyfeatures an intramolecular Diels-Alder reaction of a 5-vinyl-1,3-cyclohexadiene and acyclopropane ring opening.
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spelling doaj.art-360d1c95bd2543499ebee5fc57f40e3c2022-12-22T02:02:03ZengMDPI AGMolecules1420-30492004-04-019528729910.3390/90500287Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from CarvoneNoelia VeraIsmael NavarroIgnacio de AlfonsoAna C. CuñatConsuelo AgullóAntonio AbadThe commercially available monoterpene carvone has been efficiently convertedinto the tricyclo[3.2.1.02.7]octane and bicyclo[3.2.1]octane systems characteristic of somebiologically active compounds. The sequence used for this transformation involves as keyfeatures an intramolecular Diels-Alder reaction of a 5-vinyl-1,3-cyclohexadiene and acyclopropane ring opening.http://www.mdpi.com/1420-3049/9/5/287/CarvoneDiels-Alder reactioncyclopropane cleavage5-vinyl-13- cyclohexadienesamarium diiodidebicyclo[3.2.1]octanetricyclo[3.2.1.02.7]octane
spellingShingle Noelia Vera
Ismael Navarro
Ignacio de Alfonso
Ana C. Cuñat
Consuelo Agulló
Antonio Abad
Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone
Molecules
Carvone
Diels-Alder reaction
cyclopropane cleavage
5-vinyl-1
3- cyclohexadiene
samarium diiodide
bicyclo[3.2.1]octane
tricyclo[3.2.1.02.7]octane
title Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone
title_full Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone
title_fullStr Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone
title_full_unstemmed Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone
title_short Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone
title_sort synthesis of highly functionalised enantiopure bicyclo 3 2 1 octane systems from carvone
topic Carvone
Diels-Alder reaction
cyclopropane cleavage
5-vinyl-1
3- cyclohexadiene
samarium diiodide
bicyclo[3.2.1]octane
tricyclo[3.2.1.02.7]octane
url http://www.mdpi.com/1420-3049/9/5/287/
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