Asymmetric Synthesis of Griffipavixanthone Employing a Chiral Phosphoric Acid-Catalyzed Cycloaddition.

Catalysis Chemistry Techniques, Synthetic Models, Molecular Molecular Conformation Phosphoric Acids / chemistry Xanthones / chemical synthesis

Journal

Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056

Informations de publication

Date de publication:
09 01 2019
Historique:
pubmed: 20 12 2018
medline: 10 6 2020
entrez: 20 12 2018
Statut: ppublish

Résumé

Asymmetric synthesis of the biologically active xanthone dimer griffipavixanthone is reported along with its absolute stereochemistry determination. Synthesis of the natural product is accomplished via dimerization of a p-quinone methide using a chiral phosphoric acid catalyst to afford a protected precursor in excellent diastereo- and enantioselectivity. Mechanistic studies, including an unbiased computational investigation of chiral ion-pairs using parallel tempering, were performed in order to probe the mode of asymmetric induction.

Identifiants

DOI: 10.1021/jacs.8b12520 PMID: 30566336 PMC: PMC6475489
pubmed: 30566336
doi: 10.1021/jacs.8b12520
pmc: PMC6475489
mid: NIHMS1004571
doi:

Substances chimiques

Phosphoric Acids 0
Xanthones 0
xanthone 9749WEV0CA
phosphoric acid E4GA8884NN

Types de publication

Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.

Langues

eng

Sous-ensembles de citation

IM

Pagination

148-153

Subventions

Organisme : NIGMS NIH HHS
ID : R01 GM078240
Pays : United States
Organisme : NIGMS NIH HHS
ID : R24 GM111625
Pays : United States
Organisme : NIGMS NIH HHS
ID : R35 GM118173
Pays : United States

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Auteurs

Michael J Smith (MJ)

Department of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.
ORCID: 0000-0002-0389-6864

Kyle D Reichl (KD)

Department of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.
ORCID: 0000-0001-7779-0846

Randolph A Escobar (RA)

Department of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.

Thomas J Heavey (TJ)

Department of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.

David F Coker (DF)

Department of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.
ORCID: 0000-0001-6210-5228

Scott E Schaus (SE)

Department of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.
ORCID: 0000-0002-5877-6587

John A Porco (JA)

Department of Chemistry and Center for Molecular Discovery (BU-CMD) , Boston University , 590 Commonwealth Avenue , Boston , Massachusetts 02215 , United States.
ORCID: 0000-0002-2991-5680

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Classifications MeSH

Recherchemedicale.com › Phénomènes chimiques › Catalyse › Asymmetric Synthesis of Griffipavixanthone...
Recherchemedicale.com › Technologie, industrie et agriculture › Technologie › Technologie pharmaceutique › Techniques de chimie synthétique › Asymmetric Synthesis of Griffipavixanthone...
Recherchemedicale.com › Techniques d'investigation › Modèles théoriques › Modèles moléculaires › Asymmetric Synthesis of Griffipavixanthone...
Recherchemedicale.com › Phénomènes chimiques › Phénomènes biochimiques › Conformation moléculaire › Asymmetric Synthesis of Griffipavixanthone...
Recherchemedicale.com › Produits chimiques inorganiques › Composés du phosphore › Acides du phosphore › Acides phosphoriques › Asymmetric Synthesis of Griffipavixanthone...
Recherchemedicale.com › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérocycliques 3 noyaux › Xanthènes › Xanthones › Asymmetric Synthesis of Griffipavixanthone...