Total Synthesis of (-)-Clavicipitic Acid via γ,γ-Dimethylallyltryptophan (DMAT) and Chemoselective C-H Hydroxylation.

Carbon / chemistry Catalysis Chemistry Techniques, Synthetic Cyclization Ergot Alkaloids / chemical synthesis Hydrogen / chemistry Hydroxylation Tryptophan / chemistry

Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
21 06 2019
Historique:
pubmed: 24 5 2019
medline: 23 6 2020
entrez: 24 5 2019
Statut: ppublish

Résumé

The first total synthesis of natural (-)-clavicipitic acid from γ,γ-dimethylallyltryptophan (DMAT), its biosynthetic precursor, is described. This is done by regio- and chemoselective, remote, nondirected C(sp

Identifiants

DOI: 10.1021/acs.joc.9b00879 PMID: 31120249
pubmed: 31120249
doi: 10.1021/acs.joc.9b00879
doi:

Substances chimiques

Ergot Alkaloids 0
clavicipitic acid 0
Carbon 7440-44-0
Hydrogen 7YNJ3PO35Z
Tryptophan 8DUH1N11BX

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

8027-8034

Auteurs

Francesca Bartoccini (F)

Department of Biomolecular Sciences , University of Urbino Carlo Bo , Piazza Rinascimento 6 , 61029 Urbino , PU , Italy.
ORCID: 0000-0003-0400-7771

Silvia Venturi (S)

Department of Biomolecular Sciences , University of Urbino Carlo Bo , Piazza Rinascimento 6 , 61029 Urbino , PU , Italy.

Michele Retini (M)

Department of Biomolecular Sciences , University of Urbino Carlo Bo , Piazza Rinascimento 6 , 61029 Urbino , PU , Italy.
ORCID: 0000-0003-0218-8505

Michele Mari (M)

Department of Biomolecular Sciences , University of Urbino Carlo Bo , Piazza Rinascimento 6 , 61029 Urbino , PU , Italy.
ORCID: 0000-0002-3763-3587

Giovanni Piersanti (G)

Department of Biomolecular Sciences , University of Urbino Carlo Bo , Piazza Rinascimento 6 , 61029 Urbino , PU , Italy.
ORCID: 0000-0003-0418-7143

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Classifications MeSH

Recherchemedicale.com › Produits chimiques inorganiques › Éléments › Carbone › Total Synthesis of (-)-Clavicipitic Acid via...
Recherchemedicale.com › Phénomènes chimiques › Catalyse › Total Synthesis of (-)-Clavicipitic Acid via...
Recherchemedicale.com › Technologie, industrie et agriculture › Technologie › Technologie pharmaceutique › Techniques de chimie synthétique › Total Synthesis of (-)-Clavicipitic Acid via...
Recherchemedicale.com › Métabolisme › Cyclisation › Total Synthesis of (-)-Clavicipitic Acid via...
Recherchemedicale.com › Composés hétérocycliques › Alcaloïdes › Alcaloïdes de l'ergot › Total Synthesis of (-)-Clavicipitic Acid via...
Recherchemedicale.com › Produits chimiques inorganiques › Gaz › Hydrogène › Total Synthesis of (-)-Clavicipitic Acid via...
Recherchemedicale.com › Métabolisme › Hydroxylation › Total Synthesis of (-)-Clavicipitic Acid via...
Recherchemedicale.com › Acides aminés, peptides et protéines › Acides aminés › Acides aminés essentiels › Tryptophane › Total Synthesis of (-)-Clavicipitic Acid via...