Ieodomycins comprise a family of fatty acids derived from a marine <i>Bacillus</i> sp.. In this presentation, an enantioselective total synthesis of (+)-ieodomycin B along with its three other optical isomers is described. The key steps of the synthesis employ Keck asymmetric allylation to provide an enantiopure homoallylic alcohol, Wipf’s modification of Negishi’s carboalumination reaction, Sharpless asymmetric dihydroxylation, and Pinner reaction. In the final step, Stille cross-coupling reaction was employed to install the terminal 1,3-diene moiety. The main advantage of the present synthesis is highlighted in the introduction of the terminal 1,3-diene at the very end of the synthesis, which enables chemical diversity by the late-stage modification of the corresponding lactone. Furthermore, the synthesized compounds were evaluated for their inhibitory activities against HMG(3-hydroxy-3-methylglutaryl)-CoA reductase. The results will be described and discussed further.

Enantioselective total synthesis of (+)-ieodomycin B and its optical isomers: Synthesis and biological evaluation

2019 Fall National Meeting

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