InI3-catalyzed polyene cyclization of allenes and its application in the total synthesis of seven abietane-type diterpenoids
A novel polyene cyclization using the allene group as the initiator has been successfully developed. This methodology provides an efficient strategy for the construction of an abietane-type tricyclic skeleton with a functionalizable C2–C3 double bond and features a wide substrate scope and excellent...
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Veröffentlicht in: | Chemical science (Cambridge) 2022-11, Vol.13 (46), p.13893-13897 |
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Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A novel polyene cyclization using the allene group as the initiator has been successfully developed. This methodology provides an efficient strategy for the construction of an abietane-type tricyclic skeleton with a functionalizable C2–C3 double bond and features a wide substrate scope and excellent stereoselectivities. Potential utility of this approach has been well demonstrated by the collective total synthesis of seven abietane-type diterpenoids. Specifically, (±)-2,3-dihydroxyferruginol and (±)-2,3-dihydroxy-15,16-dinor-ent-pimar-8,11,13-triene were synthesized for the first time. |
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ISSN: | 2041-6520 2041-6539 |
DOI: | 10.1039/d2sc04229k |