Total synthesis of tubastrine and 3-dehydroxy tubastrine by microwave-assisted cross-coupling reactions
Original version
Lorentzen. M., Bayer, A., Sydnes, M.O., Jørgensen, K.B. (2015) Total synthesis of tubastrine and 3-dehydroxy tubastrine by microwave-assisted cross-coupling reactions. Tetrahedron, 71(43), 8278-8284 10.1016/j.tet.2015.09.003Abstract
The first syntheses of tubastrine and 3-dehydroxy tubastrine are described. The target compounds were prepared in four consecutive steps from commercially available starting materials. The central scaffold was formed by a microwave-assisted C–N cross-coupling reaction between 1,3-bis(tert-butoxycarbonyl)-guanidine and (E)-((4-(2-iodovinyl)-1,2-phenylene)bis(oxy))bis(tert-butyldimethylsilane) and (E)-tert-butyl(4-(2-iodovinyl)phenoxy)–dimethylsilane, respectively. The aryl vinyl iodides were obtained by a Hunsdiecker–Borodin-type reaction of aryl acrylic acids, which were easily available from trans-caffeic acid or trans-p-coumaric acid.