Enantioselective Synthesis of Leustroducsin B

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DESCRIPTION (provided by applicant): The project proposed herein is a methodology and synthetic investigation of the natural product leustroducsin B (1); a potent colony-stimulating factor inducer isolated from the culture broth of Streptomyces platensis. This research project will: 1) investigate the synthesis of the 1,3-disubstituted cyclohexane moiety via a palladium-catalyzed asymmetric allylic alkylation (AAA), 2) study the viability of constructing the 1,3-anf/ diol moiety using a zinc-catalyzed asymmetric aldol reaction, 3) investigate a catalytic, asymmetric [2,3]-Wittig rearrangement and apply it toward the alpha, beta-unsaturated lactone moiety, 4) complete the synthesis of the natural product and produce analogs to test for biological activity. The development of a practical synthesis of leustroducsin B (1) will be beneficial to the investigation of the biological activities that include inducing colony-stimulating factor production and thrombocytosis as well as augmenting host resistance in lethal infection with Escherichia coli.