Literature DB >> 28455854

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

Qiao Yan1, Martin G Banwell1, Michelle L Coote1,2, Richmond Lee1,2, Anthony C Willis1.   

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).
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

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

Mesh:

Substances:

Year:  2017        PMID: 28455854     DOI: 10.1002/asia.201700456

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  3 in total

1.  Chemoenzymatic Total Synthesis of Sorbicatechol Structural Analogues and Evaluation of Their Antiviral Potential.

Authors:  Anna Sib; Tobias M Milzarek; Alexander Herrmann; Lila Oubraham; Jonas I Müller; Andreas Pichlmair; Ruth Brack-Werner; Tobias A M Gulder
Journal:  Chembiochem       Date:  2019-11-19       Impact factor: 3.164

Review 2.  Samarium(ii) iodide-mediated reactions applied to natural product total synthesis.

Authors:  Majid M Heravi; Azadeh Nazari
Journal:  RSC Adv       Date:  2022-03-30       Impact factor: 3.361

Review 3.  Recent Advances in Sorbicillinoids from Fungi and Their Bioactivities (Covering 2016-2021).

Authors:  Xuwen Hou; Xuping Zhang; Mengyao Xue; Zhitong Zhao; Huizhen Zhang; Dan Xu; Daowan Lai; Ligang Zhou
Journal:  J Fungi (Basel)       Date:  2022-01-07
  3 in total

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