Total Synthesis of an Isatis indigotica-Derived Alkaloid Using a Biomimetic Thio-Diels–Alder Reaction
journal contributionposted on 30.05.2018 by Emma K. Davison, Paul A. Hume, Jonathan Sperry
Any type of content formally published in an academic journal, usually following a peer-review process.
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.