Asymmetric Synthesis of the Azabicyclic Core of the Stemona Alkaloids

A general strategy for the construction of the 1-azabicyclo[5.3.0]decane core of Stemona alkaloids is developed. Our diversity-oriented approach exploits 1,3-dipolar cycloaddition of five-membered cyclic nitrones to C6 olefins, followed by N−O reductive cleavage and azepine closure. The use of vario...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-04, Vol.70 (8), p.3157-3167
Main Authors: Alibés, Ramon, Blanco, Pilar, Casas, Eva, Closa, Montserrat, de March, Pedro, Figueredo, Marta, Font, Josep, Sanfeliu, Elena, Álvarez-Larena, Ángel
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Chemistry
Combinatorial Chemistry Techniques
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Organic chemistry
Preparations and properties
Stemonaceae - chemistry
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Summary:A general strategy for the construction of the 1-azabicyclo[5.3.0]decane core of Stemona alkaloids is developed. Our diversity-oriented approach exploits 1,3-dipolar cycloaddition of five-membered cyclic nitrones to C6 olefins, followed by N−O reductive cleavage and azepine closure. The use of various enantiopure pyrroline N-oxides allows for a practical, stereoselective preparation of several putative precursors of different Stemona alkaloids.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo047867q