The synthesis of bis(indole) natural products from Arundo donax was achieved. The biaryl ring system was constructed using the first ynindole Diels-Alder reaction. The alkaloids are chiral, having stable enantiomeric conformations with half-lives of racemization of t1/2 = 4150-25100 seconds at room temperature. The enantiomers were isolated and their absolute configurations were determined using the exciton chirality method.

Synthesis of bis(indole) alkaloids from Arundo donax

249th National Meeting (2015)

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