A tandem, nitroalkene conjugate addition/[3+2] cycloaddition approach to the synthesis of the pentacyclic core of (±)-scandine

被引：32
|
作者：
Denmark, Scott E. [1 ]
Cottell, Jeromy J. [1 ]
机构：
[1] Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 16-17期
关键词：
conjugate addition; 3+2] cycloaddition; nitroalkenes; quaternary stereogenic centers; silyl nitronates;
D O I：
10.1002/adsc.200600301
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The complete pentacyclic core of the melodinus alkaloid scandine has been synthesized. The synthetic strategy features two key steps: (1) a tandem nitroalkene conjugate addition/[3+2] cycloaddition of the resulting silyl nitronate and (2) an intramolecular Heck reaction of an aryl iodide with a gamma-disubstituted allylic alcohol which set a highly congested, quaternary stereogenic center with the concomitant formation of an aldehyde. Intramolecular reductive amination with this aldehyde completed the pentacyclic core.
引用
收藏
页码：2397 / 2402
页数：6
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