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Studies on the Photochemical Rearrangements of Enantiomerically Pure, Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones

Yan, Qiao; Bolte, Benoit; Bai, Yuhua; Banwell, Martin; Willis, Anthony; Carr, Paul D


A series of enantiomerically pure bicyclo[2.2.2]octenones, including the lactone-annulated system 26, has been prepared by engaging derivatives of an enzymatically derived and homochiral cis-1,2-dihydrocatechol in inter- or intra-molecular Diels–Alder reactions. Systems such as 26 readily participate in photochemically promoted oxa-di-π-methane rearrangement or 1,3-acyl migration processes to give products such as diquinane 34 or mixtures of cyclobutanone 36 and cyclopropane 38, respectively.

CollectionsANU Research Publications
Date published: 2017
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b01243


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