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Examination of Diels-Alder/Tsuji-Trost Route towards Kopsia Alkaloidsстатья
- Авторы: Zhigileva Ekaterina A., Molchanova Marina V., Solyev Pavel N., Korlukov Alexander, Baranov Mikhail S., Mikhaylov Andrey A.
- Журнал: SYNTHESIS-STUTTGART
- Год издания: 2023
- Издательство: Georg Thieme Verlag
- Местоположение издательства: Germany
- DOI: 10.1055/a-2186-7034
- Аннотация: A reaction sequence of Diels-Alder cycloaddition and Tsuji-Trost allylation was examined in terms of its application to synthesis of kopsinine and the related Kopsia alkaloids. Results of the studies in two synthetic directions are presented herein: 1) synthesis of the properly substituted diene, required for the Diels-Alder step; 2) model studies and optimization of the key reaction sequence in the absence of side-chain. Details on the challenging introduction of the side-chain into tetrahydrocarboline ketone and its silylation, resulting in rare but unproductive vinylogous Claisen cyclization, and the successful Mannich/Mukaiyama aldol sequence are disclosed for the first direction. For the second direction endo-selective Diels-Alder reaction with allyl acrylate and Tsuji-Trost allylation providing incorrect stereochemistry are discovered. Interaction of both dienes with an alkyne provides carbazoles via Alder-Rickert reaction.
- Добавил в систему: Жигилева Екатерина Андреевна