Theoretical study on the transannulation reaction of zerumbone derivatives using amine-based reagents

摘要

Zerumbone is a natural derived sesquiterpene having a unique frame structure. It has high reactivity and produces compounds with various carbon skeletons. In the reaction of a brominated zerumbone with a methylamine, a [7,1,0]bicyclic compound is formed selectively. It is predicted that this reaction begins with Michael addition, but the details are not clear, because the intermediates are not detected. To elucidate their reaction mechanisms, DFT (B3LYP/6-31G(d)) calculations were performed for the paths via and not via Michael addition.