Total synthesis of the assigned structure of (+)-Maneolactenol
The first total synthesis of the assigned structure of (+)-maneolactenol, a marine natural product, has been completed in 7 steps. The pivotal transformations involve an asymmetric Diels-Alder reaction which serves as a key step in establishing stereochemistry, and the formation of core skeleton thr...
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| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2025-06-01
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| Series: | Tetrahedron Chem |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666951X25000099 |
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| Summary: | The first total synthesis of the assigned structure of (+)-maneolactenol, a marine natural product, has been completed in 7 steps. The pivotal transformations involve an asymmetric Diels-Alder reaction which serves as a key step in establishing stereochemistry, and the formation of core skeleton through iodolactonization. Particularly noteworthy are the selective reduction of acid to aldehyde and subsequent chelation-controlled stereoselective nucleophilic addition, facilitating the rapid and efficient assembly of side-chain motifs, as well as the selective reduction of the triple bond to Z-olefin moiety for the side chain construction. This strategy enabled the scalable synthesis of over 100 mg of the target compound, highlighting its practicality for larger-scale production. |
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| ISSN: | 2666-951X |