Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N -methyleuphococcinine

The 9-azabicyclo[3.3.1]nonane ring system is present in several insect- and plant-derived alkaloids. (-)-Adaline ( ) and (+)-euphococcinine ( ), found in secretions of beetles, and (+)- -methyleuphococcinine ( ), isolated from the Colorado blue spruce , are members of this alkaloid family. Their uni...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2021, Vol.17 (1), p.28-41
Main Authors: Lima, Dimas J P, Santana, Antonio E G, Birkett, Michael A, Porto, Ricardo S
Format: Article
Language:English
Subjects:
9-azabicyclo[3.3.1]nonane
Alcohol
Alkaloids
Biological activity
Chemical ecology
Chemistry
coccinelid beetles
dipolar cycloaddition
homotropane
Infections
Pathogens
Picea pungens
Plants
Review
ring-closing metathesis
Secretions
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Summary:The 9-azabicyclo[3.3.1]nonane ring system is present in several insect- and plant-derived alkaloids. (-)-Adaline ( ) and (+)-euphococcinine ( ), found in secretions of beetles, and (+)- -methyleuphococcinine ( ), isolated from the Colorado blue spruce , 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 and the recent methodologies to obtain adaline ( ), euphococcinine ( ), and -methyleuphococcinine ( ).
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.17.4