A Modular Approach to the Asymmetric Synthesis of Cytisine

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 brom...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-02, Vol.2016 (5), p.958-964
Main Authors: Struth, Felix R., Hirschhäuser, Christoph
Format: Article
Language:English
Subjects:
Alkaloids
Asymmetric synthesis
Boronate homologation
Carbenoids
Metathesis
Modularity
Natural products
Rearrangement
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Summary: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. The asymmetric synthesis of (+)‐ and (–)‐cytisine was achieved by modular application of Matteson homologations to construct the critical asymmetric moiety which is incorporated into a versatile late stage precursor (4a). Intermediate 4a was converted into cytisine in five steps.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201501435