Chemistry of the Podocarpaceae. XL. Conversion of methyl 12-Hydroxypodocarpa-8,11,13-trien-19-oate into Methyl 13-hydroxypodocarpa-8,11,13-trien-19-oate

Methods for the conversion of methyl (+)-12-hydroxypodocarpa-8,11,13- trien-19-oate (7) into the synthetically more useful compound methyl (+)-13-methoxypodocarpa-8,11,13-trien-19-oate (8) have been investigated. In the most favourable case, the transformation has been effected in c. 57% yield by a five-stage sequence involving hydrogenolysis of the 13-amino-12-tosylate (31) with Raney nickel.