朝 euphanes 的从头不对称合成的进展。
Progress toward the De Novo Asymmetric Synthesis of Euphanes.
机构信息
Department of Chemistry, Dartmouth College, Burke Laboratory, Hanover, New Hampshire 03755, United States.
University of Florida, Genetics Institute, Gainesville, Florida 32610, United States.
出版信息
Org Lett. 2022 May 27;24(20):3686-3690. doi: 10.1021/acs.orglett.2c01299. Epub 2022 May 18.
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.
摘要
描述了 euphanes 不对称合成的进展。已制备出具有五个不同取代且电子明显不同的烯烃的 C14-去甲 euphane 体系。所采用的路线基于顺序金属环介导的环加成交叉偶联、双不对称 Brønsted 酸介导的分子内 Friedel-Crafts 烷基化以及氧化重排以建立必要的 C10 季碳原子。这些研究还发现了一种新型基于 euphane 的肝 X 受体调节剂。
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