Autoxidation of allohimachalol

Article abstract of DOI:10.1016/S0040-4020(99)00938-2

The tri-substituted (2,3)-double bond in allohimachalol (1) undergoes autoxidation in the presence of singlet molecular oxygen, resulting in tertiary and secondary allylic hydroperoxides 6 and 7. These autoxidation products may then participate in complex rearrangement reactions to yield seco-allohimachalanes, which have undergone carbon-carbon bond cleavage at the 2,3- or 3,4-positions. The observed autoxidation/rearrangement reactions of 1 in vitro would account for the biogenesis of several allohimachalanes recently reported from the medicinal plant Illicium tsangii as natural products.