期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 17, 期 -, 页码 28-41出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.17.4
关键词
9-azabicyclo[3.3.1]nonane; Coccinelid beetles; dipolar cycloaddition; homotropane; ring-closing metathesis
The study reviews the chemical ecology of ladybugs and recent methodologies for obtaining adaline, euphococcinine, and N-methyleuphococcinine.
The 9-azabicyclo[3.3.1]nonane ring system is present in several insect- and plant-derived alkaloids. (-)-Adaline (1) and (+)-euphococcinine (2), found in secretions of Coccinelid beetles, and (+)- N-methyleuphococcinine (3), isolated from the Colorado blue spruce Picea pungens, are members of this alkaloid family. Their unique bicyclic system with a quaternary stereocenter, and the potent biological activity exerted by these homotropane alkaloids, make them attractive synthetic targets. This work aims briefly to review the chemical ecology of Adalia bipunctata and the recent methodologies to obtain adaline (1), euphococcinine (2), and N-methyleuphococcinine (3).
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