Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 5, Pages 958-964Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201501435
Keywords
Asymmetric synthesis; Natural products; Alkaloids; Metathesis; Rearrangement; Carbenoids; Boronate homologation
Categories
Funding
- University of Duisburg, Germany
- Science Support Center, Essen, Germany
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The asymmetric synthesis of (+)- and (-)-cytisine starts with Matteson homologations for the construction of a chiral C3-building block. Conversion of the C3-building block into a dihydropyridone is achieved by straightforward functional group interconversions and ring closing metathesis. After bromination, this central building block was diastereospecifically converted into cytisine in five steps.
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