Synonyms:Thioketone;Thioketones;Thione;Thiones
The research focuses on the total synthesis of (()-Otonecine, a pyrrolizidine alkaloid with potential cytotoxic properties, through a Thio-Diels-Alder route to the azocine ring system. The study aimed to explore the thioketone cycloaddition approach to dihydrothiopyrans as precursors for functionalized azocine derivatives and to address synthetic challenges arising from the strong interactions between basic nitrogen and ketone carbonyl in the otonecine ring system. The successful synthesis involved key steps such as thio-Diels-Alder trapping, internal Michael addition, selective C-S bond cleavage, and a series of oxidation and elimination reactions. Chemicals used in the process included Danishefsky diene, thioketone, enone, alcohol, and various reagents for oxidation and functional group manipulation, culminating in the synthesis of racemic otonecine. The research concluded that the combination of thioketone Diels-Alder addition and desulfurization technology provided access to the otonecine ring system, overcoming regiochemical challenges and exploiting transannular interactions characteristic of the otonecine ring system.
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