Remodeling of Fumagillol: Discovery of an Oxygen-Directed Oxidative Mannich Reaction

[Image: see text] An efficient, two-step construction of highly complex alkaloid-like compounds from the natural product fumagillol is described. This approach, which mimics a biosynthetic cyclase/oxidase sequence, allows for rapid and efficient structure elaboration of the basic fumagillol scaffold...

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Autores principales: Grenning, Alexander J., Snyder, John K., Porco, John A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3927640/
https://www.ncbi.nlm.nih.gov/pubmed/24410175
http://dx.doi.org/10.1021/ol4035269
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author Grenning, Alexander J.
Snyder, John K.
Porco, John A.
author_facet Grenning, Alexander J.
Snyder, John K.
Porco, John A.
author_sort Grenning, Alexander J.
collection PubMed
description [Image: see text] An efficient, two-step construction of highly complex alkaloid-like compounds from the natural product fumagillol is described. This approach, which mimics a biosynthetic cyclase/oxidase sequence, allows for rapid and efficient structure elaboration of the basic fumagillol scaffold with a variety of readily available coupling partners. Mechanistic experiments leading to the discovery of an oxygen-directed oxidative Mannich reaction are also described.
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spelling pubmed-39276402015-01-10 Remodeling of Fumagillol: Discovery of an Oxygen-Directed Oxidative Mannich Reaction Grenning, Alexander J. Snyder, John K. Porco, John A. Org Lett [Image: see text] An efficient, two-step construction of highly complex alkaloid-like compounds from the natural product fumagillol is described. This approach, which mimics a biosynthetic cyclase/oxidase sequence, allows for rapid and efficient structure elaboration of the basic fumagillol scaffold with a variety of readily available coupling partners. Mechanistic experiments leading to the discovery of an oxygen-directed oxidative Mannich reaction are also described. American Chemical Society 2014-01-10 2014-02-07 /pmc/articles/PMC3927640/ /pubmed/24410175 http://dx.doi.org/10.1021/ol4035269 Text en Copyright © 2014 American Chemical Society
spellingShingle Grenning, Alexander J.
Snyder, John K.
Porco, John A.
Remodeling of Fumagillol: Discovery of an Oxygen-Directed Oxidative Mannich Reaction
title Remodeling of Fumagillol: Discovery of an Oxygen-Directed Oxidative Mannich Reaction
title_full Remodeling of Fumagillol: Discovery of an Oxygen-Directed Oxidative Mannich Reaction
title_fullStr Remodeling of Fumagillol: Discovery of an Oxygen-Directed Oxidative Mannich Reaction
title_full_unstemmed Remodeling of Fumagillol: Discovery of an Oxygen-Directed Oxidative Mannich Reaction
title_short Remodeling of Fumagillol: Discovery of an Oxygen-Directed Oxidative Mannich Reaction
title_sort remodeling of fumagillol: discovery of an oxygen-directed oxidative mannich reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3927640/
https://www.ncbi.nlm.nih.gov/pubmed/24410175
http://dx.doi.org/10.1021/ol4035269
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AT snyderjohnk remodelingoffumagilloldiscoveryofanoxygendirectedoxidativemannichreaction
AT porcojohna remodelingoffumagilloldiscoveryofanoxygendirectedoxidativemannichreaction

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