A Two-Step, Stereoselective Synthesis of Nine-and Ten-Membered Carbocycles from Phthalates

…, F Fernández-Nieto, MR Paleo, FJ Sardina

Index: Lobato, Ruben; Veiga, Alberte X.; Perez-Vazquez, Jaime; Fernandez-Nieto, Fernando; Paleo, M. Rita; Sardina, F. Javier Organic Letters, 2013 , vol. 15, # 16 p. 4090 - 4093

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Abstract

A two-step, stereoselective procedure for the synthesis of nine-and ten-membered carbocycles from readily available phthalates is described. A variety of dialkyl phthalates have been transformed into [6, n]-fused bicyclo systems (n= 5, 6, 7) by a dearomatization/ cyclization process and then converted into cyclonona-and cyclodecadienes through a bond cleavage reaction, whereby both processes are promoted by alkaline metals in THF.