Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry

• Type of Material: Article
• Authors: A Kong, Emory University; DE Mancheno, Emory University; N Boudet, Emory University; R Delgado, Emory University; Eric S. Andreansky, Emory University; Simon Blakey, Emory University
• Language: English
• Date: 2016-09-19
• Publisher: Royal Society of Chemistry
• Publication Version: Final Published Version
• Copyright Statement: © The Royal Society of Chemistry 2016 This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
• License: Creative Commons Attribution 3.0 Unported
• Final Published Version (URL): http://dx.doi.org/10.1039/C6SC03578G
• Title of Journal or Parent Work: Chemical Science
• Volume: 8
• Issue: 1
• Start Page: 697
• End Page: 700
• Grant/Funding Information: This research was supported by the NSF (CHE-1362502).
• Research Categories: Chemistry, General

Abstract

The first total synthesis of malagashanine, a chloroquine potentiating indole alkaloid, is presented. A highly stereoselective cascade annulation reaction was developed to generate the tetracyclic core of the Malagasy alkaloids. This chemistry is likely to be broadly applicable to the synthesis of other members of this stereochemically unique family of natural products.