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...
| Main Authors: | , , , , , |
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| Format: | info:eu-repo/semantics/article |
| Language: | English |
| Published: |
MDPI
2020
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| Subjects: | |
| Online Access: | http://hdl.handle.net/10835/8413 |
| _version_ | 1789406416515104768 |
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| author | Rosales Martínez, Antonio Enríquez, Lourdes Jaraíz, Martín Pozo Morales, Laura Rodríguez García, Ignacio Manuel Díaz Ojeda, Emilio |
| author_facet | Rosales Martínez, Antonio Enríquez, Lourdes Jaraíz, Martín Pozo Morales, Laura Rodríguez García, Ignacio Manuel Díaz Ojeda, Emilio |
| author_sort | Rosales Martínez, Antonio |
| collection | DSpace |
| 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 BF3•Et2O as activator and water as initiator. |
| format | info:eu-repo/semantics/article |
| id | oai:repositorio.ual.es:10835-8413 |
| institution | Universidad de Cuenca |
| language | English |
| publishDate | 2020 |
| publisher | MDPI |
| record_format | dspace |
| spelling | oai:repositorio.ual.es:10835-84132023-04-12T19:47:15Z 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 Manuel Díaz Ojeda, Emilio aureol tetracyclic meroterpenoids natural products synthesis 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. 2020-09-02T10:44:34Z 2020-09-02T10:44:34Z 2020-08-26 info:eu-repo/semantics/article 1660-3397 http://hdl.handle.net/10835/8413 en https://www.mdpi.com/1660-3397/18/9/441 Attribution-NonCommercial-NoDerivatives 4.0 Internacional http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess MDPI |
| spellingShingle | aureol tetracyclic meroterpenoids natural products synthesis Rosales Martínez, Antonio Enríquez, Lourdes Jaraíz, Martín Pozo Morales, Laura Rodríguez García, Ignacio Manuel 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 | aureol tetracyclic meroterpenoids natural products synthesis |
| url | http://hdl.handle.net/10835/8413 |
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