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

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

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 condit...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2020-05, Vol.83 (5), p.1721-1724
Hauptverfasser: Anstis, Daniel G, Lindsay, Ashley C, Söhnel, Tilo, Sperry, Jonathan
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.0c00166