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

页码：1065 / 1070

页数：6

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