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

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Title:	Tandem Photoisomerization and Transannular Cyclizations of Zerumbone Epoxide: A Model for Diversity-Oriented Synthesis Using Abundant Natural Products
Authors:	Biji, M Radhakrishnan, K V Lankalapalli, R S
Keywords:	photoisomerization cyclization ketones ethers molecular structure
Issue Date:	6-Aug-2021
Publisher:	American Chemical Society
Citation:	Organic Letters; 23(15): 5871-5875.
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.
URI:	https://pubs.acs.org/doi/10.1021/acs.orglett.1c01997 http://hdl.handle.net/123456789/3875
Appears in Collections:	2021

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