Even though significant advances have been made in the development of new cancer treatments, patient survival in advance stages of renal cancer still remains very poor. Thus, much effort has been invested in the discovery and development of effective treatments for this disease. Englerin A, a natural product isolated from <i>Phyllanthus</i> engleri, has been shown to selectively inhibited the growth of renal cancer cell lines. More remarkably, englerin A has been shown to induce necrotic cell death only renal cancer cell while spearing healthy kidney cells. Although many analogs of this compound have been synthesized in the recent years, most analogs focus in the SAR of functional groups located in the seven member ring and little is known about the effects of substitution about its five member ring. Herein, we present the synthesis of four new analogs of englerin a. The key step in this synthesis is the use of enzymatic resolution to afford the desired stereochemistry in good yields. This is followed by a simple 1,4-addition to obtain the desired product in good yield. These new analogs not only provide SAR information on the effects of substitution about the five member ring, but will allow access to future click chemistry.

Synthesis of four new englerin a analogs: Using enzimatic resolution to simplify synthetic pathways

253rd National Meeting (2017)

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