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A four step synthesis of violaceic acid

Author:
Cameron, Alex, Fisher, Brendan, Rizzacasa, Mark A.
Source:
Tetrahedron 2018 v.74 no.12 pp. 1203-1206
ISSN:
0040-4020
Subject:
aldehydes, chemical structure, copper, hydrolysis, iodides, phenol
Abstract:
The total synthesis of the biaryl ether natural product violaceic acid (1) in four steps is described. The steps included a SNAr reaction between phenol 7 and flouroarene 12 to afford the biaryl ether 13, selective reduction of a nitro group to an amine in the presence of an aldehyde, a Cu mediated Sandmeyer reaction and final hydrolysis to afford the target compound 1. The amine 14 was also converted into the known iodide 18 which gave impure 1 on Pd mediated hydroxide cross coupling.
Agid:
5853406