Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence

ABSTRACT: The multistep synthesis of a prenylneoflavone through a sequence of the Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis reaction has been accomplished in 5% yield over six steps starting from commercially available 3-methoxyacetophenone. The sequence is shown to be compati...

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Autores principales: Lozinski, Oleg A., Bistodeau, J., Bennetau-Pelissero, C., Khilya, Vladimir P., Shinkaruk, S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2020
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7186117/
https://www.ncbi.nlm.nih.gov/pubmed/32346184
http://dx.doi.org/10.1007/s00706-020-02584-8
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author Lozinski, Oleg A.
Bistodeau, J.
Bennetau-Pelissero, C.
Khilya, Vladimir P.
Shinkaruk, S.
author_facet Lozinski, Oleg A.
Bistodeau, J.
Bennetau-Pelissero, C.
Khilya, Vladimir P.
Shinkaruk, S.
author_sort Lozinski, Oleg A.
collection PubMed
description ABSTRACT: The multistep synthesis of a prenylneoflavone through a sequence of the Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis reaction has been accomplished in 5% yield over six steps starting from commercially available 3-methoxyacetophenone. The sequence is shown to be compatible with a Pechmann condensation which proved to be a robust and cost-effective method for the assembling of the α-pyrone core. The results open doors to a general approach to the prenylneoflavone system starting from phenol and acetophenone derivatives. GRAPHIC ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-020-02584-8) contains supplementary material, which is available to authorized users.
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spelling pubmed-71861172020-04-28 Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence Lozinski, Oleg A. Bistodeau, J. Bennetau-Pelissero, C. Khilya, Vladimir P. Shinkaruk, S. Monatsh Chem Original Paper ABSTRACT: The multistep synthesis of a prenylneoflavone through a sequence of the Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis reaction has been accomplished in 5% yield over six steps starting from commercially available 3-methoxyacetophenone. The sequence is shown to be compatible with a Pechmann condensation which proved to be a robust and cost-effective method for the assembling of the α-pyrone core. The results open doors to a general approach to the prenylneoflavone system starting from phenol and acetophenone derivatives. GRAPHIC ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-020-02584-8) contains supplementary material, which is available to authorized users. Springer Vienna 2020-04-28 2020 /pmc/articles/PMC7186117/ /pubmed/32346184 http://dx.doi.org/10.1007/s00706-020-02584-8 Text en © Springer-Verlag GmbH Austria, part of Springer Nature 2020 This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic.
spellingShingle Original Paper
Lozinski, Oleg A.
Bistodeau, J.
Bennetau-Pelissero, C.
Khilya, Vladimir P.
Shinkaruk, S.
Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence
title Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence
title_full Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence
title_fullStr Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence
title_full_unstemmed Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence
title_short Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence
title_sort assembling the prenylneoflavone system through a pechmann condensation/mitsunobu reaction/claisen rearrangement/olefin cross-metathesis sequence
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7186117/
https://www.ncbi.nlm.nih.gov/pubmed/32346184
http://dx.doi.org/10.1007/s00706-020-02584-8
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