Racemic Total Synthesis of Elmonin and Pratenone A, from Streptomyces, Using a Common Intermediate Prepared by peri-Directed C–H Functionalization

[Image: see text] The first total synthesis of elmonin and pratenone A, two complex rearranged angucyclinones from Streptomyces, is reported. Using peri-directed C–H functionalization, the key naphthalene fragment present in both synthetic targets was efficiently prepared. Coupling to two anisole-de...

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Autores principales: Uiterweerd, Michiel T., Minnaard, Adriaan J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9806855/
https://www.ncbi.nlm.nih.gov/pubmed/36533980
http://dx.doi.org/10.1021/acs.orglett.2c03449
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author Uiterweerd, Michiel T.
Minnaard, Adriaan J.
author_facet Uiterweerd, Michiel T.
Minnaard, Adriaan J.
author_sort Uiterweerd, Michiel T.
collection PubMed
description [Image: see text] The first total synthesis of elmonin and pratenone A, two complex rearranged angucyclinones from Streptomyces, is reported. Using peri-directed C–H functionalization, the key naphthalene fragment present in both synthetic targets was efficiently prepared. Coupling to two anisole-derived fragments gave access to the natural products, in which elmonin was prepared using a biomimetic spiro-ketalization.
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spelling pubmed-98068552023-01-03 Racemic Total Synthesis of Elmonin and Pratenone A, from Streptomyces, Using a Common Intermediate Prepared by peri-Directed C–H Functionalization Uiterweerd, Michiel T. Minnaard, Adriaan J. Org Lett [Image: see text] The first total synthesis of elmonin and pratenone A, two complex rearranged angucyclinones from Streptomyces, is reported. Using peri-directed C–H functionalization, the key naphthalene fragment present in both synthetic targets was efficiently prepared. Coupling to two anisole-derived fragments gave access to the natural products, in which elmonin was prepared using a biomimetic spiro-ketalization. American Chemical Society 2022-12-19 2022-12-30 /pmc/articles/PMC9806855/ /pubmed/36533980 http://dx.doi.org/10.1021/acs.orglett.2c03449 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 Uiterweerd, Michiel T.
Minnaard, Adriaan J.
Racemic Total Synthesis of Elmonin and Pratenone A, from Streptomyces, Using a Common Intermediate Prepared by peri-Directed C–H Functionalization
title Racemic Total Synthesis of Elmonin and Pratenone A, from Streptomyces, Using a Common Intermediate Prepared by peri-Directed C–H Functionalization
title_full Racemic Total Synthesis of Elmonin and Pratenone A, from Streptomyces, Using a Common Intermediate Prepared by peri-Directed C–H Functionalization
title_fullStr Racemic Total Synthesis of Elmonin and Pratenone A, from Streptomyces, Using a Common Intermediate Prepared by peri-Directed C–H Functionalization
title_full_unstemmed Racemic Total Synthesis of Elmonin and Pratenone A, from Streptomyces, Using a Common Intermediate Prepared by peri-Directed C–H Functionalization
title_short Racemic Total Synthesis of Elmonin and Pratenone A, from Streptomyces, Using a Common Intermediate Prepared by peri-Directed C–H Functionalization
title_sort racemic total synthesis of elmonin and pratenone a, from streptomyces, using a common intermediate prepared by peri-directed c–h functionalization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9806855/
https://www.ncbi.nlm.nih.gov/pubmed/36533980
http://dx.doi.org/10.1021/acs.orglett.2c03449
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