No abstract

Photoirradiation of (6E,9E)-zerumbone-2,3-epoxide afforded a diverse range of transannular cyclized products in the presence of a catalytic amount of Sc(OTf) 3 . At the behest of the geometrical isomers produced by photoirradiation, the diversity encompasses an unprecedented eudesmane core and oxo-bridged hydroxy-olefin skeletons. Structure elucidation and the stereochemical outcome of the products are described via extensive NMR analysis. The present study serves as a model for tandem photoisomerization and transannular cyclization of natural products with enone/dienone functionality.Letter pubs.acs.org/OrgLett

Zerumbone is a naturally occurring humulene type sesquiterpene, isolated from the rhizomes of Zingiber zerumbet (L.) Smith with excellent therapeutic potential and is recognized as a valuable synthon for the construction of diverse array of natural product motifs. In this review, we intended to highlight our achievements in utilizing abundant natural product zerumbone and its derivatives for the development of pharmacologically relevant molecular scaffolds. We provided an account of the transition‐metal catalyzed 1,4‐conjugate addition reactions of zerumbone and its derivatives along with palladium‐catalyzed cross‐couplings, transition metal‐based Lewis acid promoted interrupted Nazarov cyclisation reaction with substituted indoles and transannular cyclizations, photo‐induced transformations of zerumbone and its epoxide.