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Open AccessArticle

Efficient Total Synthesis of Lissodendrin B, 2-Aminoimidazole Marine Alkaloids Isolated from Lissodendoryx (Acanthodoryx) fibrosa

1
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Yushan Road 5, Qingdao 266003, China
2
Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, China
*
Author to whom correspondence should be addressed.
Mar. Drugs 2020, 18(1), 36; https://doi.org/10.3390/md18010036
Received: 30 November 2019 / Revised: 19 December 2019 / Accepted: 20 December 2019 / Published: 31 December 2019
Lissodendrin B is a 2-aminoimidazole alkaloid bearing a (p-hydroxyphenyl) glyoxal moiety that was isolated from the Indonesian sponge Lissodendoryx (Acanthodoryx) fibrosa. 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. View Full-Text
Keywords: total synthesis; Lissodendrin B; 2-aminoimidazole; marine alkaloids total synthesis; Lissodendrin B; 2-aminoimidazole; marine alkaloids
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MDPI and ACS Style

Wei, X.; Hu, X.; Yu, R.; Wan, S.; Jiang, T. Efficient Total Synthesis of Lissodendrin B, 2-Aminoimidazole Marine Alkaloids Isolated from Lissodendoryx (Acanthodoryx) fibrosa. Mar. Drugs 2020, 18, 36.

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