Dimas J P Lima1, Antonio E G Santana2, Michael A Birkett3, Ricardo S Porto1. 1. Chemistry and Biotechnology Institute, Federal University of Alagoas, 57072970, Maceió, Brazil. 2. Center of Engineering and Agrarian Science, Federal University of Alagoas, 57100-000, Rio Largo, Brazil. 3. Rothamsted Research, West Common, Harpenden, AL5 2JQ, United Kingdon.
Abstract
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).
The 9-azabicyclo[3.3.1]nonane ring system is present in several insect- and plant-derived n class="Chemical">alkaloids. (-)-Adaline (1) and (+)-euphococcinine (2), found in secretions of Coccinelid beetles, and (+)-N-methyleuphococcinine (3), isolated from the Colorado blue sprucePicea 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).
Authors: Thomas C Coombs; Maurice D Lee; Heilam Wong; Matthew Armstrong; Bo Cheng; Wenyong Chen; Alessandro F Moretto; Lanny S Liebeskind Journal: J Org Chem Date: 2008-01-03 Impact factor: 4.354