Diplodiatoxine synthesis

Compound 117 is also a key intermediate in the synthesis of diplodiatoxin, a toxin produced by Diplodia maydis on maize and responsible for cattle disease [99]. The two chiral centers present in 117 are transferred in the target compound and induce all other chiralities of this bicyclic strucmre constructed via an intramolecular Diels-Alder reaction (Scheme 11.29). 

Ichibara, A, Kawagishi, H, Tokugawa, N, Sakamura, S, Stereoselective total synthesis and stereochemistry of diplodiatoxin, a mycotoxin from Diplodia maydis. Tetrahedron Lett, 27, 1347-1350, 1986. 

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