Syntheses of (+)-cytisine, (-)-kuraramine, (-)-isokuraramine, and (-)-jussiaeiine A.
Total syntheses of (+)-cytisine, (-)-kuraramine, (-)-isokuraramine, and (-)-jussiaeiine A were achieved via a samarium diiodide-promoted reductive deamination reaction, followed by simultaneous recyclization of a proline derivative to give the corresponding delta-lactam derivative, 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
Takahashi
Rie
R
Namiki
Hidenori
H
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001392:Azocines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D003641:Deamination; D015195:Drug Design; D007454:Iodides / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D012493:Samarium / Q000737:chemistry; D013237:Stereoisomerism; D000093843:Quinolizidine Alkaloids
D000470:Alkaloids; D001392:Azocines; D007454:Iodides; D010880:Piperidines; D011725:Pyridines; D011807:Quinolizines; D012493:Samarium; C497856:jussiaeiine A; C497858:kuraramine; C004712:cytisine; D000093843:Quinolizidine Alkaloids; C409809:samarium diiodide