Asymmetric total synthesis of novel pentacyclic indole alkaloid, kopsiyunnanine E, isolated from Kopsia arborea

Mariko Kitajima; Yosuke Murakami; Nobuaki Takahashi; Yuqiu Wu; Noriyuki Kogure; Rong-Ping Zhang; Hiromitsu Takayama

doi:10.1021/ol502265q

Asymmetric total synthesis of novel pentacyclic indole alkaloid, kopsiyunnanine E, isolated from Kopsia arborea

Org Lett. 2014 Oct 3;16(19):5000-3. doi: 10.1021/ol502265q. Epub 2014 Sep 24.

Authors

Mariko Kitajima¹, Yosuke Murakami, Nobuaki Takahashi, Yuqiu Wu, Noriyuki Kogure, Rong-Ping Zhang, Hiromitsu Takayama

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Chiba University , 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan.

PMID: 25250658
DOI: 10.1021/ol502265q

Abstract

A new pentacyclic indole alkaloid, kopsiyunnanine E, was isolated from Yunnan Kopsia arborea, and its structure, which was inferred from spectroscopic data, was established by a 16-step asymmetric total synthesis that proved that the natural alkaloid was not enantiomerically pure.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Apocynaceae / chemistry*
China
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Indole Alkaloids / isolation & purification
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Stereoisomerism

Substances

Indole Alkaloids
kopsiyunnanine E