Organic Letters p. 2966 - 2969 (2013)
Update date:2022-09-26
Topics:
Morimoto, Yoshiki
Takeuchi, Eriko
Kambara, Hitomi
Kodama, Takeshi
Tachi, Yoshimitsu
Nishikawa, Keisuke
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.
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Doi:10.1021/ol7014847
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