Second-Generation Total Synthesis of Prorocentin

[Image: see text] After a recent total synthesis had resolved all issues surrounding the constitution and stereostructure of prorocentin, it was possible to devise a new approach aiming at an improved supply of this scarce marine natural product; this compound is a cometabolite of the prototypical p...

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Autores principales: Yahata, Kenzo, Zachmann, Raphael J., Fürstner, Alois
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10334468/
https://www.ncbi.nlm.nih.gov/pubmed/37358405
http://dx.doi.org/10.1021/acs.orglett.3c01720
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author Yahata, Kenzo
Zachmann, Raphael J.
Fürstner, Alois
author_facet Yahata, Kenzo
Zachmann, Raphael J.
Fürstner, Alois
author_sort Yahata, Kenzo
collection PubMed
description [Image: see text] After a recent total synthesis had resolved all issues surrounding the constitution and stereostructure of prorocentin, it was possible to devise a new approach aiming at an improved supply of this scarce marine natural product; this compound is a cometabolite of the prototypical phosphatase inhibitor okadaic acid but still awaits detailed biological profiling. The revised entry starts from 2-deoxy-d-glucose; keys to success were a telescoped hemiacetal reduction/acetal cleavage and an exquisitely selective gold/Brønsted acid-cocatalyzed spiroacetalization.
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spelling pubmed-103344682023-07-12 Second-Generation Total Synthesis of Prorocentin Yahata, Kenzo Zachmann, Raphael J. Fürstner, Alois Org Lett [Image: see text] After a recent total synthesis had resolved all issues surrounding the constitution and stereostructure of prorocentin, it was possible to devise a new approach aiming at an improved supply of this scarce marine natural product; this compound is a cometabolite of the prototypical phosphatase inhibitor okadaic acid but still awaits detailed biological profiling. The revised entry starts from 2-deoxy-d-glucose; keys to success were a telescoped hemiacetal reduction/acetal cleavage and an exquisitely selective gold/Brønsted acid-cocatalyzed spiroacetalization. American Chemical Society 2023-06-26 /pmc/articles/PMC10334468/ /pubmed/37358405 http://dx.doi.org/10.1021/acs.orglett.3c01720 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Yahata, Kenzo
Zachmann, Raphael J.
Fürstner, Alois
Second-Generation Total Synthesis of Prorocentin
title Second-Generation Total Synthesis of Prorocentin
title_full Second-Generation Total Synthesis of Prorocentin
title_fullStr Second-Generation Total Synthesis of Prorocentin
title_full_unstemmed Second-Generation Total Synthesis of Prorocentin
title_short Second-Generation Total Synthesis of Prorocentin
title_sort second-generation total synthesis of prorocentin
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10334468/
https://www.ncbi.nlm.nih.gov/pubmed/37358405
http://dx.doi.org/10.1021/acs.orglett.3c01720
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