First diastereoselective chiral synthesis of (-)-securinine.
[reaction: see text] A diastereoselective total synthesis of securinine in optically pure form was achieved by employing ring-closing metathesis of the corresponding dienyne compound as a key step.
Honda
Toshio
T
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan. honda@hoshi.ac.jp
Namiki
Hidenori
H
Kaneda
Kyosuke
K
Mizutani
Hirotake
H
D000470:Alkaloids / Q000138:chemical synthesis*; D001381:Azepines / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones / Q000138:chemical synthesis*; D008956:Models, Chemical; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones; D010875:Pipecolic Acids; D010880:Piperidines; C000785:securinine