Total Synthesis of Lytophilippine A

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The natural product lytophilippine A is a marine polyketide that was isolated from the stinging hydroid Lytocarpus philippinus. The natural product chemistry of the Red Sea hydroid has yet been sparsely investigated. The large number of chiral carbon atoms is the defining and distinguishing element of the molecular architecture of lytophilippine A, and constitutes a significant challenge for asymmetric synthesis. The original proposal for the structure of lytophilippine A was falsified by total synthesis and a revision of the assignment of the absolute configuration is required. Based on our massive experimental groundwork, this project suggests the completion of the total synthesis of the (11R,13R,14R,15R)-configured lytophilippine A and several of its (13,14,15)-diastereomers. With the completion of the total synthesis, we aim to contribute significantly to the final structural assignment and enable further investigation of the biological properties of the natural product. By selecting a target of unusual molecular complexity for our total synthesis research program, we intent to push the frontiers of the science of synthesis to the state of the art and possibly beyond.