A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation

A new concise general methodology for the synthesis of different tetracyclic meroterpenoids is reported: (±)-aureol (1), the key intermediate of this general route. The synthesis of (±)-aureol (1) was achieved in seven steps (28% overall yield) from (±)-albicanol. The key steps of this route include...

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Autores principales: Rosales Martínez, Antonio, Enríquez, Lourdes, Jaraíz, Martín, Pozo Morales, Laura, Rodríguez-García, Ignacio, Díaz Ojeda, Emilio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7551916/
https://www.ncbi.nlm.nih.gov/pubmed/32858988
http://dx.doi.org/10.3390/md18090441
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author Rosales Martínez, Antonio
Enríquez, Lourdes
Jaraíz, Martín
Pozo Morales, Laura
Rodríguez-García, Ignacio
Díaz Ojeda, Emilio
author_facet Rosales Martínez, Antonio
Enríquez, Lourdes
Jaraíz, Martín
Pozo Morales, Laura
Rodríguez-García, Ignacio
Díaz Ojeda, Emilio
author_sort Rosales Martínez, Antonio
collection PubMed
description A new concise general methodology for the synthesis of different tetracyclic meroterpenoids is reported: (±)-aureol (1), the key intermediate of this general route. The synthesis of (±)-aureol (1) was achieved in seven steps (28% overall yield) from (±)-albicanol. The key steps of this route include a C–C bond-forming reaction between (±)-albicanal and a lithiated arene unit and a rearrangement involving 1,2-hydride and 1,2-methyl shifts promoted by BF(3)•Et(2)O as activator and water as initiator.
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spelling pubmed-75519162020-10-14 A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation Rosales Martínez, Antonio Enríquez, Lourdes Jaraíz, Martín Pozo Morales, Laura Rodríguez-García, Ignacio Díaz Ojeda, Emilio Mar Drugs Article A new concise general methodology for the synthesis of different tetracyclic meroterpenoids is reported: (±)-aureol (1), the key intermediate of this general route. The synthesis of (±)-aureol (1) was achieved in seven steps (28% overall yield) from (±)-albicanol. The key steps of this route include a C–C bond-forming reaction between (±)-albicanal and a lithiated arene unit and a rearrangement involving 1,2-hydride and 1,2-methyl shifts promoted by BF(3)•Et(2)O as activator and water as initiator. MDPI 2020-08-26 /pmc/articles/PMC7551916/ /pubmed/32858988 http://dx.doi.org/10.3390/md18090441 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Rosales Martínez, Antonio
Enríquez, Lourdes
Jaraíz, Martín
Pozo Morales, Laura
Rodríguez-García, Ignacio
Díaz Ojeda, Emilio
A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation
title A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation
title_full A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation
title_fullStr A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation
title_full_unstemmed A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation
title_short A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation
title_sort concise route for the synthesis of tetracyclic meroterpenoids: (±)-aureol preparation and mechanistic interpretation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7551916/
https://www.ncbi.nlm.nih.gov/pubmed/32858988
http://dx.doi.org/10.3390/md18090441
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