A bifunctional Lewis acid induced cascade cyclization to the tricyclic core of ent-kaurenoids and its application to the formal synthesis of (±)-platensimycin.
A bifunctional Lewis acid induced cascade cyclization to the tricyclic core of ent-kaurenoids and its application to the formal synthesis of (±)-platensimycin.
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DOI：
10.1021/ol3033412
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发表时间：
2013-01
期刊：
影响因子：
5.2
通讯作者：
Lizhi Zhu;Ye-Qiang Han;Guangyan Du;Chi-Sing Lee
中科院分区：
文献类型：
--
作者：
Lizhi Zhu;Ye-Qiang Han;Guangyan Du;Chi-Sing Lee
发展了一种温和而有效的双官能团路易斯酸诱导的级联环合反应，用于构筑三环胡萝卜烯类化合物。以溴化锌为双官能团的Lewis酸，一系列取代的烯酮和二烯在室温下顺利进行级联环化反应，一锅可得三环产物，产率高(75-91%)，非对映选择性高。该环化产物已成功地用于(±)-白新霉素的合成。
A mild and efficient bifunctional Lewis acid induced cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids. With ZnBr(2) as the bifunctional Lewis acid, a series of substituted enones and dienes underwent cascade cyclization smoothly at room temperature and provided the tricyclic products in one pot with good yields (75-91%) and high diastereoselectivity. The cyclized product has been successfully employed for the formal synthesis of (±)-platensimycin.