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

Qiao Yan, Martin G. Banwell^*, Michelle L. Coote, Richmond Lee, Anthony C. Willis

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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).

Original language	English
Pages (from-to)	1480-1484
Number of pages	5
Journal	Chemistry - An Asian Journal
Volume	12
Issue number	13
DOIs	https://doi.org/10.1002/asia.201700456
Publication status	Published - 4 Jul 2017

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title = "Establishing the True Structure of the Sorbicillinoid-Derived Isolate Rezishanone C by Total Synthesis",

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",

author = "Qiao Yan and Banwell, \{Martin G.\} and Coote, \{Michelle L.\} and Richmond Lee and Willis, \{Anthony C.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2017",

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day = "4",

doi = "10.1002/asia.201700456",

language = "English",

volume = "12",

pages = "1480--1484",

journal = "Chemistry - An Asian Journal",

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T1 - Establishing the True Structure of the Sorbicillinoid-Derived Isolate Rezishanone C by Total Synthesis

AU - Yan, Qiao

AU - Banwell, Martin G.

AU - Coote, Michelle L.

AU - Lee, Richmond

AU - Willis, Anthony C.

PY - 2017/7/4

Y1 - 2017/7/4

N2 - 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).

AB - 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).

KW - Diels–Alder

KW - density functional calculations

KW - natural products

KW - sorbicillins

KW - total synthesis

UR - https://www.scopus.com/pages/publications/85020183731

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DO - 10.1002/asia.201700456

M3 - Article

SN - 1861-4728

VL - 12

SP - 1480

EP - 1484

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 13

ER -

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

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