20178-12-5Relevant articles and documents
SYNTHESIS OF MONOTERPENE OXABICYCLODIOLS STARTING FROM α-PINENE
Popova, L. A.,Biba, V.I.,Prishchepenko, V.M.,Shavyrin, S.V.,Kozlov, N.G.
, p. 1346 - 1350 (2007/10/02)
Reaction of pinol with a mixture of formic acid and hydrogen peroxide selectively yields 1,8-epoxy-p-menthane-2-endo,6-endo-diol (epomediol), while (2R, 4S)-(-)-sobrerol under these conditions yields (1R, 2R, 4R, 6R)-(+)-6,8-epoxy-p-menthane-1,2-diol.Acetylation of epomediol gives the diacetate with preservation of the structure of the starting compound.Acetylation of 6,8-epoxy-p-menthane-1,2-diol proceeds with opening of the oxide ring and formation of a mixture of (1S, 2R, 5R)-(+)-p-menth-4(8)-ene-1,2,5-triacetates.
