Total Synthesis of the Tetracyclic Antimalarial Alkaloid (±)-Myrioneurinol

被引：27
|
作者：
Nocket, Anthony J. [1 ]
Weinreb, Steven M. [1 ]
机构：
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 51期
基金：
美国国家科学基金会;
关键词：
alkaloids; Michael addition; natural products; nitrogen heterocycles; total synthesis; FUSED TRICYCLIC AMINES; MYRIONEURON-NUTANS; BIOMIMETIC SYNTHESIS; DIPOLAR CYCLOADDITION; NITRARIA ALKALOIDS; ACYCLIC ALDEHYDES; MICHAEL REACTION; (+)-ISONITRAMINE; MYRIOXAZINE; CYCLIZATION;
D O I：
10.1002/anie.201407810
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first total synthesis of the tetracyclic antimalarial Myrioneuron alkaloid (+/-)-myrioneurinol has been accomplished using three highly diastereoselective reactions as pivotal steps: 1) an intramolecular Michael addition of a benzyloxycarbonyl-protected lactam titanium enolate to an alpha,beta-unsaturated ester for construction of the spirocyclic C5 quaternary center and the a/d rings, 2) a malonate anion conjugate addition to a transient nitrosoalkene to install the requisite functionality and configuration at the C7 position, and 3) an intramolecular sulfonyliminium aza-Sakurai reaction to form the b ring and the attendant C9/C10 configuration of the natural product.
引用
收藏
页码：14162 / 14165
页数：4
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