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 (<b>1</b>), the key intermediate of this general route. The synthesis of (±)-aureol (<b>1</b>) was achieved in seven steps (28% overall yield) from (±)-albicano...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-08-01
|
| Series: | Marine Drugs |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1660-3397/18/9/441 |
| _version_ | 1797555457023279104 |
|---|---|
| author | Antonio Rosales Martínez Lourdes Enríquez Martín Jaraíz Laura Pozo Morales Ignacio Rodríguez-García Emilio Díaz Ojeda |
| author_facet | Antonio Rosales Martínez Lourdes Enríquez Martín Jaraíz Laura Pozo Morales Ignacio Rodríguez-García Emilio Díaz Ojeda |
| author_sort | Antonio Rosales Martínez |
| collection | DOAJ |
| description | A new concise general methodology for the synthesis of different tetracyclic meroterpenoids is reported: (±)-aureol (<b>1</b>), the key intermediate of this general route. The synthesis of (±)-aureol (<b>1</b>) 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<sub>3</sub>•Et<sub>2</sub>O as activator and water as initiator. |
| first_indexed | 2024-03-10T16:47:46Z |
| format | Article |
| id | doaj.art-60c48512c5c24d419e26216fd8846aa4 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T16:47:46Z |
| publishDate | 2020-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-60c48512c5c24d419e26216fd8846aa42023-11-20T11:26:38ZengMDPI AGMarine Drugs1660-33972020-08-0118944110.3390/md18090441A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic InterpretationAntonio Rosales Martínez0Lourdes Enríquez1Martín Jaraíz2Laura Pozo Morales3Ignacio Rodríguez-García4Emilio Díaz Ojeda5Department of Chemical Engineering, Escuela Politécnica Superior, University of Sevilla, 41011 Sevilla, SpainDepartment of Electricity and Electronics, University of Valladolid, 47011 Valladolid, SpainDepartment of Electricity and Electronics, University of Valladolid, 47011 Valladolid, SpainDepartment of Chemical Engineering, Escuela Politécnica Superior, University of Sevilla, 41011 Sevilla, SpainOrganic Chemistry, CeiA3, University of Almería, 04120 Almería, SpainDepartment of Chemical Engineering, Escuela Politécnica Superior, University of Sevilla, 41011 Sevilla, SpainA new concise general methodology for the synthesis of different tetracyclic meroterpenoids is reported: (±)-aureol (<b>1</b>), the key intermediate of this general route. The synthesis of (±)-aureol (<b>1</b>) 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<sub>3</sub>•Et<sub>2</sub>O as activator and water as initiator.https://www.mdpi.com/1660-3397/18/9/441aureoltetracyclic meroterpenoidsnatural products synthesis |
| spellingShingle | Antonio Rosales Martínez Lourdes Enríquez Martín Jaraíz Laura Pozo Morales Ignacio Rodríguez-García Emilio Díaz Ojeda A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation Marine Drugs aureol tetracyclic meroterpenoids natural products synthesis |
| 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 | https://www.mdpi.com/1660-3397/18/9/441 |
| work_keys_str_mv | AT antoniorosalesmartinez aconciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation AT lourdesenriquez aconciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation AT martinjaraiz aconciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation AT laurapozomorales aconciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation AT ignaciorodriguezgarcia aconciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation AT emiliodiazojeda aconciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation AT antoniorosalesmartinez conciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation AT lourdesenriquez conciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation AT martinjaraiz conciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation AT laurapozomorales conciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation AT ignaciorodriguezgarcia conciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation AT emiliodiazojeda conciserouteforthesynthesisoftetracyclicmeroterpenoidsaureolpreparationandmechanisticinterpretation |