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Establishing the True Structure of the Sorbicillinoid-Derived Isolate Rezishanone C by Total Synthesis

Yan, Qiao; Banwell, Martin; Coote, Michelle; Lee, Zhong (Richmond); Willis, Anthony

Description

The enantiomer, ent-4, of the true structure, 4, of the sorbicillinoid rezishanone C (sorbivinetone) has been synthesized from a homochiral cis-1,2-dihydrocatechol that is itself generated through the whole-cell biotransformation of toluene. These studies together with dispersion-corrected DFT calculations support the proposal that rezishanone C is an artefact of the isolation process and arises through a Diels-Alder reaction between ethyl vinyl ether and sorbicillinol (3).

CollectionsANU Research Publications
Date published: 2017
Type: Journal article
URI: http://hdl.handle.net/1885/159289
Source: Chemistry - An Asian Journal
DOI: 10.1002/asia.201700456

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