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

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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.

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

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Supplementary files

Article information


Submitted
10 Aug 2016
Accepted
11 Sep 2016
First published
19 Sep 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 697-700
Article type
Edge Article

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

A. Kong, D. E. Mancheno, N. Boudet, R. Delgado, E. S. Andreansky and S. B. Blakey, Chem. Sci., 2017, 8, 697
DOI: 10.1039/C6SC03578G

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