In the Soderberg research laboratory, a palladium-catalyzed reductive N-heterocyclization has emerged as a powerful tool for the synthesis of a variety of functionalized indoles. To elaborate more on its application in natural products synthesis, our recent efforts are focused on the synthesis of tricyclic azepinoindoles. These unique types of natural products share a common azepino(5,4,3-<i>cd</i>) indole framework also found in communesins, a family of alkaloids that have been extensively investigated mainly due to their cytotoxicity. We have completed total syntheses of two naturally occurring azepinoindole alkaloids, hyrtioreticulin C and D starting from a commercially available acetophenone derivative. The key azepinoindole skeleton was assembled via an intramolecular Mizoroki-Heck reaction followed by a palladium-catalyzed reductive N-heterocyclization. Syntheses of two other azepinoindole alkaloids, aurantioclavine and clavicipitic acid using similar strategies are currently underway.

Total synthesis of four tricyclic azepinoindole alkaloids: Aurantioclavine, clavicipitic acid and hyrtioreticulin C and D

254th National Meeting (2017)

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