Total Synthesis of the 2,5-Disubstituted γ-Pyrone E1 UAE Inhibitor Himeic Acid A.

Pyrones / pharmacology Fatty Acids, Unsaturated Alkylation Ubiquitin-Activating Enzymes / metabolism

Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
20 10 2023
Historique:
medline: 23 10 2023
pubmed: 6 10 2023
entrez: 6 10 2023
Statut: ppublish

Résumé

The first total synthesis of the E1 ubiquitin-activating enzyme inhibitor, himeic acid A, is reported. A McCombie reaction was used to form the core γ-pyrone via a 6π-electrocyclization. A dioxenone ring-opening/acyl ketene trapping reaction with a primary amide provided the unusual unsymmetrical imide functionality. Other key steps include the use of an Evans auxiliary alkylation (d.r. ≥ 95:5) to install the (

Identifiants

DOI: 10.1021/acs.orglett.3c02761 PMID: 37801638
pubmed: 37801638
doi: 10.1021/acs.orglett.3c02761
doi:

Substances chimiques

himeic acid A 0
Pyrones 0
Fatty Acids, Unsaturated 0
Ubiquitin-Activating Enzymes EC 6.2.1.45

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

7502-7506

Auteurs

Heyuan Lu (H)

Davenport Research Laboratories, Dept. of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada.

Kishor L Handore (KL)

Davenport Research Laboratories, Dept. of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada.
ORCID: 0000-0001-5956-0238

Tabitha E Wood (TE)

Davenport Research Laboratories, Dept. of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada.
Princess Margaret Cancer Centre, University Health Network, 101 College Street, Toronto, ON M5G 1L7, Canada.
ORCID: 0000-0002-5433-6883

Grace K Shimokura (GK)

Davenport Research Laboratories, Dept. of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada.
ORCID: 0000-0003-1975-653X

Aaron D Schimmer (AD)

Princess Margaret Cancer Centre, University Health Network, 101 College Street, Toronto, ON M5G 1L7, Canada.

Robert A Batey (RA)

Davenport Research Laboratories, Dept. of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada.
Acceleration Consortium, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada.
ORCID: 0000-0001-8808-7646

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Classifications MeSH

questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Pyrannes › Pyrones › Total Synthesis of the 2,5-Disubstituted...
questionsmedicales.fr › Lipides › Acides gras › Acides gras insaturés › Total Synthesis of the 2,5-Disubstituted...
questionsmedicales.fr › Métabolisme › Alkylation › Total Synthesis of the 2,5-Disubstituted...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Ligases › Ubiquitin-protein ligase complexes › Ubiquitin-activating enzymes › Total Synthesis of the 2,5-Disubstituted...