Progress toward the De Novo Asymmetric Synthesis of Euphanes

被引：2

作者：

Wai, HtooTint ^{[1
]}

Koelblen, Thomas ^{[2
]}

Hayes, Matthew E. ^{[2
]}

Burris, Thomas P. ^{[2
]}

Micalizio, Glenn C. ^{[1
]}

机构：

[1] Dartmouth Coll, Dept Chem, Hanover, NH 03755 USA

[2] Univ Florida, Genet Inst, Gainesville, FL 32610 USA

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 20期

基金：

美国国家卫生研究院;

关键词：

CYCLIZATION; TERPENES; DECALINS; STEROIDS; AGONISTS;

D O I：

10.1021/acs.orglett.2c01299

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 Bronsted 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.

引用

页码：3686 / 3690

页数：5

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