Asymmetric Total Synthesis of Pentacyclic Indole Alkaloid Andranginine and Absolute Configuration of Natural Product Isolated from Kopsia arborea

Shino Tooriyama; Yuji Mimori; Yuqiu Wu; Noriyuki Kogure; Mariko Kitajima; Hiromitsu Takayama

doi:10.1021/acs.orglett.7b01076

Asymmetric Total Synthesis of Pentacyclic Indole Alkaloid Andranginine and Absolute Configuration of Natural Product Isolated from Kopsia arborea

Org Lett. 2017 May 19;19(10):2722-2725. doi: 10.1021/acs.orglett.7b01076. Epub 2017 May 8.

Authors

Shino Tooriyama¹, Yuji Mimori¹, Yuqiu Wu¹, Noriyuki Kogure¹, Mariko Kitajima¹, Hiromitsu Takayama¹

Affiliation

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

PMID: 28481107
DOI: 10.1021/acs.orglett.7b01076

Abstract

The first asymmetric total synthesis of andranginine (1) via an asymmetric Morita-Baylis-Hillman reaction and a diastereoselective intramolecular Diels-Alder reaction has revealed that natural andranginine (1) isolated from Kopsia arborea existed as a scalemic mixture and contained predominantly the (16R,21S) form rather than the (16S,21R) form.

Publication types

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

MeSH terms

Biological Products
Indole Alkaloids / chemical synthesis*
Magnoliopsida
Molecular Structure
Stereoisomerism

Substances

Biological Products
Indole Alkaloids
andranginine