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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:
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
Descripción
Sumario: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.