Total Synthesis of Lamellarins D, H, and R and Ningalin B

被引：126

作者：

Li, Qingjiang ^{[1
]}

Jiang, Jingqian ^{[1
]}

Fan, Aili ^{[1
]}

Cui, Yuxin ^{[1
]}

Jia, Yanxing ^{[1
,2
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Media, State Key Lab Drug Res, Shanghai 201203, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 02期

基金：

中国国家自然科学基金;

关键词：

G TRIMETHYL ETHER; HYPERVALENT IODINE(III) REAGENT; IMINIUM SALT DERIVATIVES; BIARYL COUPLING REACTION; MARINE NATURAL-PRODUCTS; EFFICIENT SYNTHESIS; ALPHA; 20-SULFATE; LUKIANOL-A; ALKALOIDS; PYRROLES;

D O I：

10.1021/ol1027877

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise total synthesis of lamellarins D (7 steps), H (7 steps), and R (5 steps) and ningalin B (5 steps) is achieved starting from the corresponding aldehydes and amines. The synthesis features three oxidative reactions as key steps in a biomimetic manner, involving an AgOAc-mediated oxidative coupling reaction to construct the pyrrole core, a Pb(OAc)(4)-induced oxidative cyclization to form the lactone, and Kita's oxidation reaction to form the pyrrole-arene C-C bond.

引用

收藏

页码：312 / 315

页数：4

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