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

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About: Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence Goto Sponge NotDistinct Permalink

An Entity of Type : schema:ScholarlyArticle, within Data Space : wasabi.inria.fr associated with source document(s)

Attributes	Values
type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
title	Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence
Creator	Bennetau-Pelissero, · Bistodeau, · Khilya, Vladimir Lozinski, Oleg Shinkaruk, ·
source	Medline; PMC
abstract	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.
has issue date	2020-04-28(xsd:dateTime)
bibo:doi	10.1007/s00706-020-02584-8
bibo:pmid	32346184
has license	no-cc
sha1sum (hex)	aae68bf07bed536b0199e63ce9580bc7ae2ad36b
schema:url	https://doi.org/10.1007/s00706-020-02584-8
resource representing a document's title	Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis sequence
has PubMed Central identifier	PMC7186117
has PubMed identifier	32346184
schema:publication	Monatsh Chem
resource representing a document's body	covid:aae68bf07bed536b0199e63ce9580bc7ae2ad36b#body_text
is schema:about of	named entity 'Claisen rearrangement' named entity 'sequence' named entity 'The sequence' named entity 'general' named entity 'open doors' named entity 'Pechmann condensation' named entity 'Claisen rearrangement' named entity 'olefin' named entity 'starting' named entity 'neoflavone' named entity 'synthon' named entity 'prenyl' named entity 'olefin' named entity '5.2' named entity 'Bruker' named entity 'olefin' named entity 'cinnamates' named entity 'sulfuric acid' named entity 'boron trichloride' named entity 'potassium hydroxide' named entity 'resorcinol' named entity 'H NMR' named entity 'naturally occurring' named entity 'substrate' named entity 'mmol' named entity 'ethers' named entity 'Grubbs catalyst' named entity 'aromatic rings' named entity 'EtOAc' named entity 'ppm' named entity 'aromatic compounds' named entity 'starting material' named entity 'Acetylation' named entity 'bond cleavage' named entity 'allyl group' named entity 'SARS-CoV' named entity 'structural modification' named entity 'α-pyrone' named entity 'olefin' named entity 'HCl' named entity 'acetone' named entity 'papain' named entity 'Angiotensin-converting enzyme (ACE) inhibitors' named entity 'acetyl chloride' named entity 'CH 3' named entity '2-methyl-2-butene' named entity 'THF' named entity 'H NMR' named entity 'ppm' named entity 'pH 1' named entity 'prenylation' named entity 'prenyl group' named entity 'olefin' named entity 'allyl' named entity 'alkylation' named entity 'olefin' named entity 'Mitsunobu reaction' named entity 'olefin' named entity 'retrosynthesis' named entity 'CDCl' named entity 'ppm' named entity 'neoflavone' named entity 'activity profile' named entity 'Prenyl group' named entity 'Diethyl carbonate' named entity 'bioactivity' named entity 'chloroform' named entity 'acetone' named entity 'ppm' named entity 'phenols' named entity 'motif' named entity 'aromatic ring' named entity 'DCM' named entity 'argon' named entity 'sodium hydride' named entity 'acetone' named entity 'neoflavone'

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