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.