Indole alkaloids are a diversely distributed and significant family of natural products. Due to their structural complexity and biological properties, these natural products and their medicinal properties remain of great interest. The oxindole alkaloids fall into the important group of monoterpene indole alkaloids which contain the oxindole moiety. Depending on the structural complexity, these alkaloids exhibit important biological activity. The total synthesis of these alkaloids are challenging in both a stereospecific and enantiospecific manner. In this poster the first total synthesis of the macroline related oxindoles, <b>macrogentine</b> and <b>alstonoxine A </b>will be described. The enantiospecific synthesis begins from commercially available D-(+)-tryptophan, the key steps of which included the asymmetric Pictet-Spengler reaction, diastereospecific oxidative-rearrangement of the tetrahydro-β-carboline and stereospecific enolate-mediated palladium-catalyzed cross coupling process.

Stereospecific total synthesis of macroline-related oxindoles: Macrogentine and alstonoxine A

251st National Meeting (2016)

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