Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis

[Image: see text] Chiral diamine-derived hydrogen-bond donors were evaluated for their ability to effect stereocontrol in an intramolecular hetero-Diels–Alder (HDA) reaction hypothesized in the biosynthesis of brevianamides A and B. Collectively, these results provide proof of principle that small-m...

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Autores principales: Sprague, Daniel J., Nugent, Benjamin M., Yoder, Ryan A., Vara, Brandon A., Johnston, Jeffrey N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4339957/
https://www.ncbi.nlm.nih.gov/pubmed/25697748
http://dx.doi.org/10.1021/ol503626w
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author Sprague, Daniel J.
Nugent, Benjamin M.
Yoder, Ryan A.
Vara, Brandon A.
Johnston, Jeffrey N.
author_facet Sprague, Daniel J.
Nugent, Benjamin M.
Yoder, Ryan A.
Vara, Brandon A.
Johnston, Jeffrey N.
author_sort Sprague, Daniel J.
collection PubMed
description [Image: see text] Chiral diamine-derived hydrogen-bond donors were evaluated for their ability to effect stereocontrol in an intramolecular hetero-Diels–Alder (HDA) reaction hypothesized in the biosynthesis of brevianamides A and B. Collectively, these results provide proof of principle that small-molecule hydrogen-bond catalysis, if even based on a hypothetical biosynthesis construct, holds significant potential within enantioselective natural product synthesis.
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spelling pubmed-43399572015-02-26 Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis Sprague, Daniel J. Nugent, Benjamin M. Yoder, Ryan A. Vara, Brandon A. Johnston, Jeffrey N. Org Lett [Image: see text] Chiral diamine-derived hydrogen-bond donors were evaluated for their ability to effect stereocontrol in an intramolecular hetero-Diels–Alder (HDA) reaction hypothesized in the biosynthesis of brevianamides A and B. Collectively, these results provide proof of principle that small-molecule hydrogen-bond catalysis, if even based on a hypothetical biosynthesis construct, holds significant potential within enantioselective natural product synthesis. American Chemical Society 2015-01-31 2015-02-20 /pmc/articles/PMC4339957/ /pubmed/25697748 http://dx.doi.org/10.1021/ol503626w Text en Copyright © 2015 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Sprague, Daniel J.
Nugent, Benjamin M.
Yoder, Ryan A.
Vara, Brandon A.
Johnston, Jeffrey N.
Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis
title Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis
title_full Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis
title_fullStr Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis
title_full_unstemmed Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis
title_short Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis
title_sort adaptation of a small-molecule hydrogen-bond donor catalyst to an enantioselective hetero-diels–alder reaction hypothesized for brevianamide biosynthesis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4339957/
https://www.ncbi.nlm.nih.gov/pubmed/25697748
http://dx.doi.org/10.1021/ol503626w
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