Biomimetic epoxide-opening cascades of oxasqualenoids triggered by hydrolysis of the terminal epoxide.

The biomimetic epoxide-opening cascades from squalene polyepoxides 4–6 to triterpene polyethers (oxasqualenoids) teurilene (1), glabrescol (2), and omaezakianol (3), respectively, were reproduced in a single event by chemical reaction. These cascades proceeded through the 5-exo tandem cyclization triggered by Bronsted acid-catalyzed hydrolysis of the terminal epoxide, mimicking the direct hydrolysis mechanism of epoxide hydrolases.