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Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition.
The Journal of Antibiotics ( IF 3.3 ) Pub Date : 2018-Feb-01 , DOI: 10.1038/ja.2017.91
Shuichi Hagihara , Kengo Hanaya , Takeshi Sugai , Mitsuru Shoji

Englerin A, a guaiane sesquiterpene isolated from Phyllanthus engleri, showed highly potent and selective growth inhibitory activities against renal cancer cell lines. We synthesized the key tricyclic intermediate from commercially available 2,2-dimethyl-1,3-dioxan-5-one via regio- and diastereoselective [4+3] cycloaddition between the formyl enol silyl ether and the disubstituted furan, in 4.8% total yield over 10 steps.

中文翻译:

利用区域选择性和非对映选择性的[4 + 3]环加成法来合成englerinA。

Englerin A,一种从卷柏(Phyllanthus engleri)分离出的愈创树倍半萜烯,对肾癌细胞具有高度有效的选择性生长抑制活性。我们通过甲酰基烯醇甲硅烷基醚与二取代呋喃之间的区域和非对映选择性[4 + 3]环加成反应,由市售的2,2-二甲基-1,3-二恶烷-5-酮合成了关键的三环中间体,总计4.8%产量超过10个步骤。
更新日期:2017-08-02
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