Regioselective 1,2-Diol Rearrangement by Controlling the Loading of BF3·Et2O and Its Application to the Synthesis of Related Nor-Sesquiterene- and Sesquiterene-Type Marine Natural Products
The regiocontrolled rearrangement of 1,2-diols has been achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new lig...
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| Veröffentlicht in: | Organic letters 2017-07, Vol.19 (14), p.3811-3814 |
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| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | The regiocontrolled rearrangement of 1,2-diols has been achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new light is shed on piancol-type rearrangements that will be useful in diversity-oriented synthesis of related natural products. |
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| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/acs.orglett.7b01679 |