閉環メタセシスおよびPayne転位を利用したCJ-12,950の合成研究　

抄録

CJ-12,950 and CJ-13,357 are 12-membered salicylic macrolactone compounds, isolated from a zygomycete Mortierella verticillata, but their stereostructures have not been determined. These lactones have been reported to potently induce the LDL receptor gene in vitro, by enhancing LDL receptor expression in human hepatocytes 2-fold at 100 nM. Consequently, they have potential relevance to the treatment of hypercholesterolemia and hyperlipidemia. We planned to develop an efficient synthetic route to the compounds, including elucidation of their stereostructures, using ring-closing metathesis (RCM) and Payne rearrangement as key steps. We have succeeded in constructing the E/Z-12-membered macrolactone structures of the target compounds by means of RCM, which are possible precursors to attempt regioselective epoxidation and subsequent Payne rearrangement.

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