Enantioselective Synthesis of Cryptopleurine and Boehmeriasin A via Organocatalytic Intramolecular Aza-Michael Addition

被引：20
|
作者：
Zeng, Chuanqi
Liu, Hanbin
Zhang, Mengyao
Guo, Jiajia
Jiang, Shunchao
Yu, Shouyun [1 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Analyt Chem Life Sci, Nanjing 210093, Jiangsu, Peoples R China
来源：
SYNLETT | 2012年 / 15期
基金：
中国国家自然科学基金; 高等学校博士学科点专项科研基金;
关键词：
alkaloids; enantioselectivity; ketones; Michael addition; total synthesis; ASYMMETRIC-SYNTHESIS; ALKALOIDS; (-)-ANTOFINE; COMPOUND; PROLINE;
D O I：
10.1055/s-0031-1290457
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective synthesis of phenanthroquinolizidine alkaloids cryptopleurine and boehmeriasin A was achieved in eight steps from commercial available Cbz-protected 2-piperidinone in 22% and 20% overall yield, respectively. The key steps of this route are intramolecular enantioselective aza-Michael addition, intramolecular aldol addition, and oxidative coupling.
引用
收藏
页码：2251 / 2254
页数：4
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