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Progress toward the De Novo Asymmetric Synthesis of Euphanes
HtooTint Wai1, Thomas Koelblen2, Matthew E Hayes2
1Department of Chemistry, Dartmouth College, Burke Laboratory, Hanover, New Hampshire 03755, United States.
Abstract:
Progress toward an asymmetric synthesis of euphanes is described. A C14-desmethyl euphane system possessing five differentially substituted and electronically distinct alkenes has been prepared. The route employed is based on sequential metallacycle-mediated annulative cross-coupling, double asymmetric Brønsted acid mediated intramolecular Friedel-Crafts alkylation, and an oxidative rearrangement to establish the requisite C10 quaternary center. These studies have also led to the discovery of a novel euphane-based modulator of the Liver X Receptor.
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