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A Modular Approach to the Asymmetric Synthesis of Cytisine
Author(s) -
Struth Felix R.,
Hirschhäuser Christoph
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501435
Subject(s) - cytisine , chemistry , block (permutation group theory) , halogenation , metathesis , combinatorial chemistry , ring closing metathesis , modular design , ring (chemistry) , stereochemistry , organic chemistry , computer science , biochemistry , geometry , receptor , nicotinic agonist , mathematics , polymerization , operating system , polymer
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.