Concise enantiospecific synthesis of a coccinellied alkaloid, (-)-adalinine.
[reaction: see text] An enantiospecific synthesis of a coccinellied alkaloid, (-)-adalinine, was established starting from (S)-(-)-pyroglutamic acid, where a stereoselective Michael addition and a samarium iodide-promoted regioselective carbon-nitrogen bond cleavage reaction were involved as the key reactions.
Honda
T
T
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan. honda@hoshi.ac.jp
Kimura
M
M
D000818:Animals; D001517:Coleoptera / Q000737:chemistry*; D006868:Hydrolysis; D007202:Indicators and Reagents; D010880:Piperidines / Q000138:chemical synthesis*; D012493:Samarium; D013237:Stereoisomerism
D007202:Indicators and Reagents; D010880:Piperidines; C418568:adalinine; D012493:Samarium