Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products

[Image: see text] Herein, we describe a two-step ring expansion of 1-indanones to afford 2-chloro/bromo-1-naphthols (32 examples). The developed method shows broad functional group tolerance, benefits from mild reaction conditions, and enables rapid access to the tetracyclic core of gilvocarcin natu...

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Autores principales: Zamarija, Ivica, Marsh, Benjamin J., Magauer, Thomas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7612072/
https://www.ncbi.nlm.nih.gov/pubmed/34780199
http://dx.doi.org/10.1021/acs.orglett.1c03530
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author Zamarija, Ivica
Marsh, Benjamin J.
Magauer, Thomas
author_facet Zamarija, Ivica
Marsh, Benjamin J.
Magauer, Thomas
author_sort Zamarija, Ivica
collection PubMed
description [Image: see text] Herein, we describe a two-step ring expansion of 1-indanones to afford 2-chloro/bromo-1-naphthols (32 examples). The developed method shows broad functional group tolerance, benefits from mild reaction conditions, and enables rapid access to the tetracyclic core of gilvocarcin natural products. The orthogonally functionalized products allow for selective postmodifications as exemplified in the total synthesis of defucogilvocarcin M. For the selective oxidation of the chromene, a mild and regioselective oxidation protocol (DDQ and TBHP) was developed.
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spelling pubmed-76120722021-12-04 Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products Zamarija, Ivica Marsh, Benjamin J. Magauer, Thomas Org Lett [Image: see text] Herein, we describe a two-step ring expansion of 1-indanones to afford 2-chloro/bromo-1-naphthols (32 examples). The developed method shows broad functional group tolerance, benefits from mild reaction conditions, and enables rapid access to the tetracyclic core of gilvocarcin natural products. The orthogonally functionalized products allow for selective postmodifications as exemplified in the total synthesis of defucogilvocarcin M. For the selective oxidation of the chromene, a mild and regioselective oxidation protocol (DDQ and TBHP) was developed. American Chemical Society 2021-11-15 2021-12-03 /pmc/articles/PMC7612072/ /pubmed/34780199 http://dx.doi.org/10.1021/acs.orglett.1c03530 Text en © 2021 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 Zamarija, Ivica
Marsh, Benjamin J.
Magauer, Thomas
Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products
title Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products
title_full Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products
title_fullStr Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products
title_full_unstemmed Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products
title_short Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products
title_sort ring expansion of 1-indanones to 2-halo-1-naphthols as an entry point to gilvocarcin natural products
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7612072/
https://www.ncbi.nlm.nih.gov/pubmed/34780199
http://dx.doi.org/10.1021/acs.orglett.1c03530
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AT magauerthomas ringexpansionof1indanonesto2halo1naphtholsasanentrypointtogilvocarcinnaturalproducts

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