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 (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).

Morita-Baylis-Hillman adducts and their derivatives: a patent-based exploration of diverse biological activities.

Morita-Baylis-Hillman adducts are polyfunctionalized compounds that result from a three-component reaction involving an electrophilic sp2 carbon (aldehyde, ketone or imine) and the α-position of an activated alkene, catalyzed by a tertiary amine. These adducts exhibit a wide range of biological activities and act as valuable starting materials for developing drug candidates, pesticides, polymers, and other applications. In this regard, the present review aimed to explore the biological potential of Morita-Baylis-Hillman adducts and their derivatives as documented in patent literature. Additionally, the review delves into the synthetic methodologies employed in their preparation.