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: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-08-01
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| Series: | Marine Drugs |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1660-3397/18/9/441 |
| Summary: | 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. |
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| ISSN: | 1660-3397 |