Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative

The stereoselective Diels–Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C(2)-...

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Detalles Bibliográficos
Autores principales: Tabuchi, Toshiki, Urabe, Daisuke, Inoue, Masayuki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3629056/
https://www.ncbi.nlm.nih.gov/pubmed/23616810
http://dx.doi.org/10.3762/bjoc.9.74
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author Tabuchi, Toshiki
Urabe, Daisuke
Inoue, Masayuki
author_facet Tabuchi, Toshiki
Urabe, Daisuke
Inoue, Masayuki
author_sort Tabuchi, Toshiki
collection PubMed
description The stereoselective Diels–Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C(2)-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine.
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spelling pubmed-36290562013-04-24 Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative Tabuchi, Toshiki Urabe, Daisuke Inoue, Masayuki Beilstein J Org Chem Full Research Paper The stereoselective Diels–Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C(2)-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine. Beilstein-Institut 2013-04-04 /pmc/articles/PMC3629056/ /pubmed/23616810 http://dx.doi.org/10.3762/bjoc.9.74 Text en Copyright © 2013, Tabuchi et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Tabuchi, Toshiki
Urabe, Daisuke
Inoue, Masayuki
Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative
title Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative
title_full Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative
title_fullStr Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative
title_full_unstemmed Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative
title_short Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative
title_sort asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3629056/
https://www.ncbi.nlm.nih.gov/pubmed/23616810
http://dx.doi.org/10.3762/bjoc.9.74
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