Asymmetric Total Synthesis of (-)-Leuconoxine via Chiral Phosphoric Acid Catalyzed Desymmetrization of a Prochiral Diester

被引：43
|
作者：
Higuchi, Kazuhiro [1 ]
Suzuki, Shin [1 ]
Ueda, Reeko [1 ]
Oshima, Norifumi [1 ]
Kobayashi, Emiko [1 ]
Tayu, Masanori [1 ]
Kawasaki, Tomomi [1 ]
机构：
[1] Meiji Pharmaceut Univ, Tokyo 2048588, Japan
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 01期
关键词：
INDOLE ALKALOIDS; MELODININE E; LEUCONOXINE; CYCLIZATION; MERSICARPINE; YLIDES;
D O I：
10.1021/ol5033865
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The asymmetric total synthesis of (-)-leuconoxine has been achieved. The desymmetrization of a prochiral diester using a chiral phosphoric acid catalyst produced a highly enantioenriched lactam with excellent yield. The ring construction featuring an intramolecular N-acyliminium cyclization and the one-step pyrrolidone formation using Bestmanns ylide was successfully accomplished.
引用
收藏
页码：154 / 157
页数：4
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