Madangamines are a group of cytotoxic alkaloids that are found in marine sponges that belongs to the order of Haplosclerida. The Madangamines have a common ABC diazatricyclic core which has been of much synthetic interest. In this work the common diazatricyclic core of Madangamine has been synthesized in overall 17% yield in 17 steps with all the proper functional groups present at the required positions to complete the synthesis of Madangamines. The key step in this synthesis is the PIFA (Phenyliodine(III) bis(trifluoroacetate)) mediated regioselective oxamidation reaction to form the azabicyclic core, which joins the ring A. This transformation is anticipated to proceed via a <i>N</i>-acyl-<i>N</i>-alkoxy aziridinium ion formed by addition of a singlet nitrenium ion on the alkene in ring C.

Nitrenium-ion-mediated oxamidation to synthesize the common diazatricyclic core of madangamine

251st National Meeting (2016)

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