Diazanorbornene: A Valuable Synthon towards Carbocycles and Heterocycles

Abstract

Desymmetrization of meso compounds is well recognized as a powerful method for delivering biologically relevant molecular skeletons in a few synthetic steps. Heterobicyclic olefins are a class of meso compounds which exhibit exceptional reactivity due to their high ring strain originating from the unfavorable bond angles and eclipsing interactions. Extensive research was carried out towards the synthetic transformations of oxa-, aza-, and diazanorbornenes/norbornadienes for the synthesis of a wide variety of carbocycles and heterocycles in a

Transition Metal/Lewis Acid Catalyzed Reactions of Zerumbone for Diverse Molecular Motifs

“…[21] The utility of Sc(OTf) 3 as a catalyst was employed in ring expansion during synthesis of the epi-ilimaquinone core. [22] In our group, Sc(OTf) 3 was utilized extensively in synthetic transformations of highly strained bicyclic systems [23] and zerumbone (1, Scheme 1), an eleven-membered monocyclic sesquiterpenoid, to diverse polycyclic skeletal motifs.…”