Toward an integrated route to the vernonia allenes and related sesquiterpenoids

The synthesis of a model endocyclic allene related to the vernonia allenes is described. Fragmentation of a suitable decalin derivative gave the simplified germacrane scaffold. Computational analysis of this and related substrates provides insight into the stereoelectronic requirements of C–C fragme...

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Detalles Bibliográficos
Autores principales: Xu, Da, Drahl, Michael A, Williams, Lawrence J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3135329/
https://www.ncbi.nlm.nih.gov/pubmed/21804888
http://dx.doi.org/10.3762/bjoc.7.104
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author Xu, Da
Drahl, Michael A
Williams, Lawrence J
author_facet Xu, Da
Drahl, Michael A
Williams, Lawrence J
author_sort Xu, Da
collection PubMed
description The synthesis of a model endocyclic allene related to the vernonia allenes is described. Fragmentation of a suitable decalin derivative gave the simplified germacrane scaffold. Computational analysis of this and related substrates provides insight into the stereoelectronic requirements of C–C fragmentation. The overall strategy to access these and other sesquiterpenes and the key steps in the present sequence are also discussed.
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spelling pubmed-31353292011-07-29 Toward an integrated route to the vernonia allenes and related sesquiterpenoids Xu, Da Drahl, Michael A Williams, Lawrence J Beilstein J Org Chem Letter The synthesis of a model endocyclic allene related to the vernonia allenes is described. Fragmentation of a suitable decalin derivative gave the simplified germacrane scaffold. Computational analysis of this and related substrates provides insight into the stereoelectronic requirements of C–C fragmentation. The overall strategy to access these and other sesquiterpenes and the key steps in the present sequence are also discussed. Beilstein-Institut 2011-07-05 /pmc/articles/PMC3135329/ /pubmed/21804888 http://dx.doi.org/10.3762/bjoc.7.104 Text en Copyright © 2011, Xu 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 Letter
Xu, Da
Drahl, Michael A
Williams, Lawrence J
Toward an integrated route to the vernonia allenes and related sesquiterpenoids
title Toward an integrated route to the vernonia allenes and related sesquiterpenoids
title_full Toward an integrated route to the vernonia allenes and related sesquiterpenoids
title_fullStr Toward an integrated route to the vernonia allenes and related sesquiterpenoids
title_full_unstemmed Toward an integrated route to the vernonia allenes and related sesquiterpenoids
title_short Toward an integrated route to the vernonia allenes and related sesquiterpenoids
title_sort toward an integrated route to the vernonia allenes and related sesquiterpenoids
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3135329/
https://www.ncbi.nlm.nih.gov/pubmed/21804888
http://dx.doi.org/10.3762/bjoc.7.104
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