Organic Chemistry - Tandem Photoisomerization and Transannular Cyclizations of Zerumbone Epoxide: A Model for Diversity-Oriented Synthesis using Abundant Natural Products  

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Tandem Photoisomerization and Transannular Cyclizations of Zerumbone Epoxide: A Model for Diversity-Oriented Synthesis using Abundant Natural Products

Mohanan Biji, Kokkuvayil Vasu Radhakrishnan* and Ravi Shankar Lankalapalli*

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.

Organic Letters 2021. DOI: 10.1021/acs.orglett.1c01997

 

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