Asperazine is a compound that has recently been isolated from a sponge that lives in the Carribbean Sea. Asperazine has only been isolated one time in small amounts, but from the minute quantities available, biological testing indicated that asperazine exhibited both high potency and selectivity for destroying leukemia cells. The combination of its impressive initial biological activity, scarcity in nature, and complex chemical structure makes asperazine an attractive candidate for total synthesis. In addition to synthesizing asperazine itself, this synthetic route will allow for the synthesis of a substantial number of analogues for the purpose of developing a structure-activity relationship (SAR). The synthetic route is outlined herein. Key steps will include a catalytic, diastereoselective Heck reaction to set a crowded quaternary center, and an Overman rearrangement to ultimately generate an amino acid functional group. This proposed route is concise and involves novel applications of the Heck reaction and Overman rearrangement. This synthesis will supply valuable material to aid in the development of potential anticancer agents.
