Enantioselective total synthesis of atisane diterpenoids: (+)-sapinsigin H, (+)-agallochaol C, and (+)-16α, 17-dihydroxy-atisan-3-one.
In: Chemical communications (Cambridge, England), 2024-06-07
academicJournal
Zugriff:
Enantioselective total synthesis of (+)-sapinsigin H, (+)-agallochaol C, and (+)-16α, 17-dihydroxy-atisan-3-one has been accomplished starting from enantiopure Wieland-Miescher ketone. Key features of the syntheses include a benzannulation step to construct the tricyclic core, an oxidative dearomatization step to generate the diene, and a Diels-Alder reaction with ethylene gas to establish the bicyclo[2.2.2]octane framework. Efficient late-stage functionalisation of the A-ring by aerobic oxidation and Baeyer-Villiger oxidation completed the atisane target molecules.
Titel: |
Enantioselective total synthesis of atisane diterpenoids: (+)-sapinsigin H, (+)-agallochaol C, and (+)-16α, 17-dihydroxy-atisan-3-one.
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Autor/in / Beteiligte Person: | Dethe, DH ; Sharma, N ; Juyal, S ; Singh, P ; Siddiqui, SA |
Zeitschrift: | Chemical communications (Cambridge, England), 2024-06-07 |
Veröffentlichung: | Ahead of Print, 2024 |
Medientyp: | academicJournal |
ISSN: | 1364-548X (electronic) |
DOI: | 10.1039/d4cc01982b |
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