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A four step synthesis of violaceic acid
- Cameron, Alex, Fisher, Brendan, Rizzacasa, Mark A.
- Tetrahedron 2018 v.74 no.12 pp. 1203-1206
- aldehydes, chemical structure, copper, hydrolysis, iodides, phenol
- 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.