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Marine Drugs
Volume 18
Issue 9
10.3390/md18090441
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Article

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

by
Antonio Rosales Martínez
1,*,
Lourdes Enríquez
2,
Martín Jaraíz
2,
Laura Pozo Morales
1,
Ignacio Rodríguez-García
3 and
Emilio Díaz Ojeda
1
1
Department of Chemical Engineering, Escuela Politécnica Superior, University of Sevilla, 41011 Sevilla, Spain
2
Department of Electricity and Electronics, University of Valladolid, 47011 Valladolid, Spain
3
Organic Chemistry, CeiA3, University of Almería, 04120 Almería, Spain
*
Author to whom correspondence should be addressed.
Mar. Drugs 2020, 18(9), 441; https://doi.org/10.3390/md18090441
Received: 30 July 2020 / Revised: 23 August 2020 / Accepted: 25 August 2020 / Published: 26 August 2020
(This article belongs to the Special Issue Synthesis of Marine Natural Products and Molecules Inspired by Marine Substances)
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Abstract

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 BF3•Et2O as activator and water as initiator. View Full-Text
Keywords: aureol; tetracyclic meroterpenoids; natural products synthesis aureol; tetracyclic meroterpenoids; natural products synthesis
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MDPI and ACS Style

Rosales Martínez, A.; Enríquez, L.; Jaraíz, M.; Pozo Morales, L.; Rodríguez-García, I.; Díaz Ojeda, E. A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation. Mar. Drugs 2020, 18, 441. https://doi.org/10.3390/md18090441

AMA Style

Rosales Martínez A, Enríquez L, Jaraíz M, Pozo Morales L, Rodríguez-García I, Díaz Ojeda E. A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation. Marine Drugs. 2020; 18(9):441. https://doi.org/10.3390/md18090441

Chicago/Turabian Style

Rosales Martínez, Antonio, Lourdes Enríquez, Martín Jaraíz, Laura Pozo Morales, Ignacio Rodríguez-García, and Emilio Díaz Ojeda. 2020. "A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation" Marine Drugs 18, no. 9: 441. https://doi.org/10.3390/md18090441

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