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

Qiao Yan; Martin G Banwell; Michelle L Coote; Richmond Lee; Anthony C Willis

doi:10.1002/asia.201700456

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

Chem Asian J. 2017 Jul 4;12(13):1480-1484. doi: 10.1002/asia.201700456. Epub 2017 Jun 5.

Authors

Qiao Yan¹, Martin G Banwell¹, Michelle L Coote^{1

2}, Richmond Lee^{1

2}, Anthony C Willis¹

Affiliations

¹ Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT, 2601, Australia.
² ARC Centre of Excellence for Electromaterials Science.

PMID: 28455854
DOI: 10.1002/asia.201700456

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).

Keywords: Diels-Alder; density functional calculations; natural products; sorbicillins; total synthesis.

MeSH terms

Cycloaddition Reaction
Cyclohexanones / chemistry*
Ethyl Ethers / chemistry*
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Heterocyclic Compounds, 4 or More Rings / isolation & purification*
Molecular Structure
Quantum Theory
Stereoisomerism

Substances

Cyclohexanones
Ethyl Ethers
Heterocyclic Compounds, 4 or More Rings
sorbicillinol
ethyl vinyl ether