Total Synthesis of Penicyclone A Using a Double Grignard Reaction

[Image: see text] We describe the first total synthesis of penicyclone A, a novel deep-sea fungus-derived polyketide, and a reevaluation of its antimicrobial activity. The synthesis of this unique spirolactone was achieved in 10 steps starting from a known d-ribose derivative. The key steps include...

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Autores principales: Talajić, Gregor, Topić, Edi, Meštrović, Jerko, Cindro, Nikola
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9724088/
https://www.ncbi.nlm.nih.gov/pubmed/36383733
http://dx.doi.org/10.1021/acs.joc.2c02200
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author Talajić, Gregor
Topić, Edi
Meštrović, Jerko
Cindro, Nikola
author_facet Talajić, Gregor
Topić, Edi
Meštrović, Jerko
Cindro, Nikola
author_sort Talajić, Gregor
collection PubMed
description [Image: see text] We describe the first total synthesis of penicyclone A, a novel deep-sea fungus-derived polyketide, and a reevaluation of its antimicrobial activity. The synthesis of this unique spirolactone was achieved in 10 steps starting from a known d-ribose derivative. The key steps include a double Grignard reaction for the diastereoselective construction of the chiral tertiary alcohol intermediate, tandem oxidation/cyclization, and photooxygenation, followed by an oxidative rearrangement to introduce the enone functionality.
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spelling pubmed-97240882022-12-07 Total Synthesis of Penicyclone A Using a Double Grignard Reaction Talajić, Gregor Topić, Edi Meštrović, Jerko Cindro, Nikola J Org Chem [Image: see text] We describe the first total synthesis of penicyclone A, a novel deep-sea fungus-derived polyketide, and a reevaluation of its antimicrobial activity. The synthesis of this unique spirolactone was achieved in 10 steps starting from a known d-ribose derivative. The key steps include a double Grignard reaction for the diastereoselective construction of the chiral tertiary alcohol intermediate, tandem oxidation/cyclization, and photooxygenation, followed by an oxidative rearrangement to introduce the enone functionality. American Chemical Society 2022-11-16 2022-12-02 /pmc/articles/PMC9724088/ /pubmed/36383733 http://dx.doi.org/10.1021/acs.joc.2c02200 Text en © 2022 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 Talajić, Gregor
Topić, Edi
Meštrović, Jerko
Cindro, Nikola
Total Synthesis of Penicyclone A Using a Double Grignard Reaction
title Total Synthesis of Penicyclone A Using a Double Grignard Reaction
title_full Total Synthesis of Penicyclone A Using a Double Grignard Reaction
title_fullStr Total Synthesis of Penicyclone A Using a Double Grignard Reaction
title_full_unstemmed Total Synthesis of Penicyclone A Using a Double Grignard Reaction
title_short Total Synthesis of Penicyclone A Using a Double Grignard Reaction
title_sort total synthesis of penicyclone a using a double grignard reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9724088/
https://www.ncbi.nlm.nih.gov/pubmed/36383733
http://dx.doi.org/10.1021/acs.joc.2c02200
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