A Bifunctional Lewis Acid Induced Cascade Cyclization to the Tricyclic Core of ent-Kaurenoids and Its Application to the Formal Synthesis of (±)-Platensimycin

被引：19

作者：

Zhu, Lizhi ^{[1
]}

Han, Yejian ^{[1
]}

Du, Guangyan ^{[1
]}

Lee, Chi-Sing ^{[1
]}

机构：

[1] Peking Univ, Lab Chem Genom, Sch Chem Biol & Biotechnol, Shenzhen Univ Town,Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 03期

基金：

中国国家自然科学基金;

关键词：

ANTIBACTERIAL PROPERTIES; ENANTIOSELECTIVE ROUTE; OXATETRACYCLIC CORE; PLATENSIMYCIN; PLATENCIN; ANALOGS; (-)-PLATENSIMYCIN; EFFICIENT; FABF; IDENTIFICATION;

D O I：

10.1021/ol3033412

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient bifunctional Lewis acid induced cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenolds. With ZnBr2 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 (+/-)-platenslmycln.

引用

页码：524 / 527

页数：4

共 10 条

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