Autoxidation of allohimachalol

✍ Scribed by Koon-Sin Ngo; Geoffrey D. Brown

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 898 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00938-2

✦ Synopsis

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 seccallohimachahutes, which have undergone carbon-carbon bond cleavage at the 2,3-or 3,4-positions. The observed autoxidationkearrangement reactions of 1 in Vito would account for the biogenesis of several allohimachalanes recently reported from the medicinal plant Illicium tsungii as natural products.