Stereochemistry of reduction of umbellulone (thuj-3-en-2-one) and isodihydroumbellulone (4βH-thujan-2-one)

Abstract

The configurations of 4βH-thujan-2-one (isodihydroumbellulone) and the two 4βH-thujan-2-ols (neoiso- and iso-dihydroumbellulols) have been determined by ¹H and ¹³C n.m.r. spectroscopy. Based on these data, the reduction of the title compounds by metal hydrides and alkoxides has been shown to be consistent with control of stereoselectivity by the reactant conformation.