Formal Syntheses of (±)-Platensimycin and (±)-Platencin via a Dual-Mode Lewis Acid Induced Cascade Cyclization Approach

被引：42

作者：

Zhu, Lizhi ^{[1
]}

Zhou, Congshan ^{[1
,2
]}

Yang, Wei ^{[1
]}

He, Shuzhong ^{[1
]}

Cheng, Gui-Juan ^{[1
]}

Zhang, Xinhao ^{[1
]}

Lee, Chi-Sing ^{[1
]}

机构：

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

[2] Hunan Inst Sci & Technol, Coll Chem & Chem Engn, Yueyang 414006, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 16期

基金：

中国国家自然科学基金;

关键词：

EFFECTIVE CORE POTENTIALS; ZETA VALENCE QUALITY; MAIN-GROUP ELEMENTS; MOLECULAR CALCULATIONS; ANTIBACTERIAL PROPERTIES; ENANTIOSELECTIVE ROUTE; ASYMMETRIC-SYNTHESIS; OXATETRACYCLIC CORE; TRICYCLIC CORE; BASIS-SETS;

D O I：

10.1021/jo401105q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient dual-mode Lewis acid induced Diels Alder (DA)/carbocyclization cascade cyclizadon reaction has been developed for construction of the tricyclic core of ent-kaurenoids in one pot with the aid of a theoretical study on the it,c-Lewis acidities of a variety of Lewis acids. With ZnBr2 as the dual-mode Lewis acid, a series of substituted enones and dienes underwent DA/carbocyclization cascade cyclization reaction smoothly at room temperature and provided the tricyclic cyclized products in one pot with good yields and high diastereoselectivity. The tricyclic cyclized product has been successfully utilized as a common intermediate for formal syntheses of (+/-)-platensimycin and (+/-)-platencin.

引用

页码：7912 / 7929

页数：18

共 120 条

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