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Progress toward the De Novo Asymmetric Synthesis of Euphanes.

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.

SUBMITTER: Wai H

PROVIDER: S-EPMC9419992 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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Progress toward the De Novo Asymmetric Synthesis of Euphanes.

Wai HtooTint H Koelblen Thomas T Hayes Matthew E ME Burris Thomas P TP Micalizio Glenn C GC

Organic letters 20220518 20

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 ...[more]

PMID: 35584298

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