Establishing the True Structure of the Sorbicillinoid-Derived Isolate Rezishanone C by Total Synthesis
Date
2017
Authors
Yan, Qiao
Banwell, Martin
Coote, Michelle
Lee, Zhong (Richmond)
Willis, Anthony
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Wiley-VCH Verlag GMBH
Abstract
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).
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Chemistry - An Asian Journal
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Journal article
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Open Access
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