Asymmetric Total Synthesis of (-)-Lundurine B and Determination of Its Absolute Stereochemistry

被引：22
|
作者：
Nakajima, Masaya [1 ]
Arai, Shigeru [1 ]
Nishida, Atsushi [1 ]
机构：
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuou ku, Chiba 2608675, Japan
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2015年 / 10卷 / 04期
关键词：
alkaloids; asymmetric synthesis; lundurine; natural products; total synthesis; LAPIDILECTA ALKALOID (+/-)-LAPIDILECTINE-B; SAMARIUM DIIODIDE; CYCLOPROPYL MOIETY; CARBONYL-COMPOUNDS; ALLYLIC AMINATION; KOPSIA ALKALOIDS; INDOLE ALKALOIDS; (+/-)-LUNDURINE; TENUIS; SYSTEM;
D O I：
10.1002/asia.201403407
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A total synthesis of the Kopsia tenuis alkaloid (-)-lundurine B has been achieved. A quaternary chiral carbon has been created by an asymmetric deprotonation using a symmetric spiro cyclohexanone intermediate with a chiral lithium amide. The hexacyclic skeleton was sequentially constructed through metal-mediated reactions. The absolute stereochemistry of intermediate 5 has been unambiguously established by X-ray crystallographic analysis. This is the first description of the absolute stereochemistry of Kopsia tenuis alkaloids based on chemical synthesis.
引用
收藏
页码：1065 / 1070
页数：6
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