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Org Lett. 2013 Jun 21;15(12):2966-9. doi: 10.1021/ol401081e. Epub 2013 May 30.

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

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  • 1Department of Chemistry, Graduate School of Science, Osaka City University , Sumiyoshi-ku, Osaka 558-8585, Japan.

Abstract

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 Brønsted acid-catalyzed hydrolysis of the terminal epoxide, mimicking the direct hydrolysis mechanism of epoxide hydrolases.

PMID:
23721415
DOI:
10.1021/ol401081e
[PubMed - indexed for MEDLINE]
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