Aza-Cope Rearrangement–Mannich Cyclizations for the Formation of Complex Tricyclic Amines: Stereocontrolled Total Synthesis of (±)-Gelsemine

A detailed examination of the use of aza-Cope rearrangement–Mannich cyclization sequences for assembling the azatricyclo[4.4.0.0(2,8)]decane core of gelsemine is described. Iminium ions and N-acyloxyiminium ions derived from endo-oriented 1-methoxy- or 1-hydroxybicyclo[2.2.2]oct-5-enylamines do not...

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Main Authors: Earley, William G., Jacobsen, Jon E., Madin, Andrew, Meier, G. Patrick, O’Donnell, Christopher J., Oh, Taeboem, Old, David W., Overman, Larry E., Sharp, Matthew J.
Formato: Artigo
Idioma:Inglês
Publicado: 2005
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Article
Acceso en liña:https://ncbi.nlm.nih.gov/pmc/articles/PMC2570375/
https://ncbi.nlm.nih.gov/pubmed/16366556
https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1021/ja055710p
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