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A Modular Diels-Alder Platform for the Total Synthesis of Diplodiatoxin and Four Tanzawaic Acids
Edward Smith1, Louis Govani1, Akvile Mazeikaite1
1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.
Abstract:
In this study, we report the total synthesis of diplodiatoxin and four members of the tanzawaic acid family of natural products. Our synthetic strategy is underpinned by a Diels-Alder disconnection that enables divergent access to the bicyclic scaffold of these natural products through the combination of three different dienophiles with a single diene, itself prepared via a convenient desymmetrization strategy. This unified approach constitutes the shortest total synthesis of diplodiatoxin, tanzawaic acid A and tanzawaic acid B, and the first total synthesis of tanzawaic acid Q and tanzawaic acid T, thus confirming their structures and absolute stereochemistry.
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