DITERPENES OF GOODENIA RAMELII F MUELL

The ether extract of Goodenia ramelii has yielded 19-(β-carboxy-n-propionyloxy)(-)-kaur-16-en-3α-ol (I) and a new diterpene triol shown to be (14R)-8β,13-epoxyeperuan-14,15,18-triol (III). The 14-epimer of III was obtained from stereoselective reaction of osmium tetroxide with 18-hydroxy-13-epi-(-)-manoyl oxide (VI) and the configuration of the 14-position firmly established. Unexpectedly the major product from reaction of osmium tetroxide with 13-epi-(-)-manoyl oxide requires approach of the reagent from the opposite side of the vinyl group to the side predominately attacked during epoxidation with perbenzoic acid. © 1968.