Tetrahedron p. 14623 - 14634 (1999)
Update date:2022-08-03
Topics:
Ngo, Koon-Sin
Brown, Geoffrey D.
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.
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