Zinc–acetic acid reductions in the lanost-8-ene-1,7,11-trione series
Abstract
Treatment of lanosta-2,8-diene-1,7,11-trione with zinc dust in boiling acetic acid affords the 8b,9a- and 8a,9b-isomers of lanost-2-ene-1,7,11-trione. Treatment of 1,7,11-trioxolanost-8-en-3b-yl acetate with zinc and acetic acid yields 8b,9a-lanost-2-ene-1,7,11-trione and the 3-epimers of 1,7,11-trioxo-8b,9a-lanostan-3-yl acetate. Epimerisation of the 3-acetate also occurs in the presence of acetyl chloride.