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Total Synthesis of an Isatis indigotica-Derived Alkaloid Using a Biomimetic Thio-Diels–Alder Reaction

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journal contribution
posted on 30.05.2018 by Emma K. Davison, Paul A. Hume, Jonathan Sperry
A biomimetic thio-Diels–Alder reaction between a dienylthiadiazole and 3-thioisatin leads to the Isatis indigotica-derived alkaloid (1), along with its diastereomer 2. This synthetic study, supported by molecular modeling, establishes the viability of the proposed biosynthesis by thio-Diels–Alder cycloaddition, a very rare reaction in nature. Moreover, the results described infer that the diastereomer 2 is an as-yet undiscovered natural product present in Isatis indigotica.