Removal of the E-Olefin Barrier of Humulene Leading to Unnatural Terpenoid-like Skeletons.

Org Lett

Graduate School of Pharmaceutical Sciences , Tohoku University, Aoba, Aramaki, Aoba-ku , Sendai 980-8578 , Japan.

Published: November 2018

An unnatural terpenoid scaffold containing a bicyclo[5.4.0]undecane moiety, as well as a salvialane skeleton based on an intramolecular C-C bond formation strategy were synthesized. Such a strategy was made possible by the removal of strained E-olefin conformations of the humulene skeleton. Some compounds were identified to show PPARα antagonist activity.

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Source
http://dx.doi.org/10.1021/acs.orglett.8b03259DOI Listing

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