Synthesis of (5R, 7S, 13S)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane

Article abstract of DOI:10.1016/0957-4166(96)00227-3

The synthesis of (5R, 7S, 13S)- and (5S, 7S, 13S)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3] pentadecane from tri-O-acetyl-D-glucal, by a convenient homologation of C-1 and C-6 atoms which led to an appropriate dihydroxyl intermediate 7, is reported. The key steps for the construction of the two spiroacetal systems involved a double, step by step, radical abstraction promoted by (diacetoxyiodo)benzene and iodine.