| Summary: | Lissodendrin B is a 2-aminoimidazole alkaloid bearing a (<i>p</i>-hydroxyphenyl) glyoxal moiety that was isolated from the Indonesian sponge <i>Lissodendoryx (Acanthodoryx) fibrosa.</i> We reported the first efficient total synthesis of Lissodendrin B. The precursor 4,5-disubstituted imidazole was obtained through Suzuki coupling and Sonogashira coupling reactions from 4-iodoimidazole. C2-azidation and reduction of the azide then provided the core structures of Lissodendrin B. Subsequent triple-bond oxidation, demethylation, and deacetylation gave the final product. The synthesis approach consists of ten steps with an overall yield of 1.1% under mild reaction conditions, and it can be applied for future analog synthesis and biological studies.
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