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A DDQ-mediated ring-opening and aromatization cascade of a tetrahydrocarbazole-fused tetrahydrofuran for the synthesis of olivacine

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dc.creator Dilek, Ömer
dc.creator Ertürk, Erkan
dc.creator Patir, Süleyman
dc.creator TİLKİ, Tahir
dc.date 2023-07-11T00:00:00Z
dc.date.accessioned 2025-02-25T10:34:52Z
dc.date.available 2025-02-25T10:34:52Z
dc.identifier 9acbf999-87c9-4f31-b9ba-aff405999689
dc.identifier 10.1016/j.tetlet.2023.154603
dc.identifier https://avesis.sdu.edu.tr/publication/details/9acbf999-87c9-4f31-b9ba-aff405999689/oai
dc.identifier.uri http://acikerisim.sdu.edu.tr/xmlui/handle/123456789/100697
dc.description It is introduced that an N-MOM-tetrahydrocarbazole-fused tetrahydrofuran is a new intermediate for the synthesis of olivacine. Upon treatment with DDQ in a mixture of H2O-THF at 80 °C, it undergoes ring-opening, MOM-removal and aromatization in one pot to yield 1-methyl-carbazole-2-ethanol, an already known precursor for olivacine. Besides, several common transformations, such as α-alklylation of N-MOM-protected tetrahydrocarbazole-1-one with ethyl bromoacetate and reduction of a lactone to tetrahydrofuran with Red-Al, have been made good use.
dc.language eng
dc.rights info:eu-repo/semantics/closedAccess
dc.title A DDQ-mediated ring-opening and aromatization cascade of a tetrahydrocarbazole-fused tetrahydrofuran for the synthesis of olivacine
dc.type info:eu-repo/semantics/article


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