Synthesis of the 1,2,4-Thiadiazole Alkaloid Polyaurine B.

Acylation Alkaloids / chemistry Molecular Structure Thiadiazoles / chemical synthesis

Journal

Journal of natural products
ISSN: 1520-6025
Titre abrégé: J Nat Prod
Pays: United States
ID NLM: 7906882

Informations de publication

Date de publication:
22 05 2020
Historique:
pubmed: 17 4 2020
medline: 30 7 2021
entrez: 17 4 2020
Statut: ppublish

Résumé

A short synthesis of the natural product polyaurine B is described. The 1,2,4-thiadiazole heterocycle was assembled using a Cu(II)-mediated heterocyclization reaction that forges the N-S bond. The final acylation step to install the methylcarbamate must be conducted under anhydrous, nonbasic conditions to prevent thiadiazole ring opening initiated by attack of hydroxide at C-5.

Identifiants

DOI: 10.1021/acs.jnatprod.0c00166 PMID: 32297745
pubmed: 32297745
doi: 10.1021/acs.jnatprod.0c00166
doi:

Substances chimiques

Alkaloids 0
Thiadiazoles 0

Types de publication

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

Langues

eng

Sous-ensembles de citation

IM

Pagination

1721-1724

Auteurs

Daniel G Anstis (DG)

School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand.

Ashley C Lindsay (AC)

School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand.

Tilo Söhnel (T)

School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand.

Jonathan Sperry (J)

School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand.
ORCID: 0000-0001-7288-3939

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Classifications MeSH

questionsmedicales.fr › Métabolisme › Acylation › Synthesis of the 1,2,4-Thiadiazole Alkaloid...
questionsmedicales.fr › Composés hétérocycliques › Alcaloïdes › Synthesis of the 1,2,4-Thiadiazole Alkaloid...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Synthesis of the 1,2,4-Thiadiazole Alkaloid...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Azoles › Thiazoles › Thiadiazoles › Synthesis of the 1,2,4-Thiadiazole Alkaloid...