A number of indole diterpenoid analogs have been discovered from fungal sclerotia. Among the indole diterpenoids, aflavinines have never yielded the total synthesis to organic chemists for decades. For the total synthesis of aflavinine, we planned a retrosynthetic strategy featuring a tandem Diels-Alder reaction as the key step. We want to develop the tandem Diels-Alder reaction that would provide a powerful access to the subtarget, the pentacycle. Followed by a convergent synthesis of the key substrate by combining three easily available fragments, attempts of tandem Diels-Alder reaction are demonstrated.

Synthetic access toward the total synthesis of aflavinine

251st National Meeting (2016)

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