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

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 o...

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Autores principales: Kong, A., Mancheno, D. E., Boudet, N., Delgado, R., Andreansky, E. S., Blakey, S. B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5297967/
https://www.ncbi.nlm.nih.gov/pubmed/28451219
http://dx.doi.org/10.1039/c6sc03578g
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author Kong, A.
Mancheno, D. E.
Boudet, N.
Delgado, R.
Andreansky, E. S.
Blakey, S. B.
author_facet Kong, A.
Mancheno, D. E.
Boudet, N.
Delgado, R.
Andreansky, E. S.
Blakey, S. B.
author_sort Kong, A.
collection PubMed
description 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.
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spelling pubmed-52979672017-04-27 Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry Kong, A. Mancheno, D. E. Boudet, N. Delgado, R. Andreansky, E. S. Blakey, S. B. Chem Sci Chemistry 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. Royal Society of Chemistry 2017-01-01 2016-09-19 /pmc/articles/PMC5297967/ /pubmed/28451219 http://dx.doi.org/10.1039/c6sc03578g Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ 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.
spellingShingle Chemistry
Kong, A.
Mancheno, D. E.
Boudet, N.
Delgado, R.
Andreansky, E. S.
Blakey, S. B.
Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry
title Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry
title_full Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry
title_fullStr Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry
title_full_unstemmed Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry
title_short Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry
title_sort total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5297967/
https://www.ncbi.nlm.nih.gov/pubmed/28451219
http://dx.doi.org/10.1039/c6sc03578g
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