Description
Aplysin, isolated from the sea hare Aplysia kurodai, is representative of a class of halogenated sesquiterpenoids, which exhibits antifeedant properties to protect the host mollusks from raptorial advances. The sterically congested structure of Aplysin, containing two consecutive quaternary carbon stereocenters, has attracted considerable synthetic interest.
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Uses
Aplysin is a brominated sesquiterpene with an isoprene backbone that exhibits hepatoprotective, immunomodulatory, and antitumor activities. Aplysin effectively prevents spontaneous pancreatic necrosis and inflammatory responses in NOD mice[1].
Synthesis
The enantioselective formal total synthesis of aplysin has been achieved utilizing a palladium-catalyzed addition of arylboronic acid to the allenic alcohol followed by the Eschenmoser/Claisen rearrangement as the key steps.
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References
[1] Liu Y, et al. Aplysin retards pancreatic necrosis and inflammatory responses in NOD Mice by stabilizing intestinal barriers and regulating gut microbial composition[J]. Mediators of Inflammation, 2020, 2020(1): 1280130. DOI:
10.1155/2020/1280130[1] MASAHIRO YOSHIDA Kozo S Yasunobu Shoji. Enantioselective formal total synthesis of aplysin utilizing a palladium-catalyzed addition of an arylboronic acid to an allenic alcohol—Eschenmoser/Claisen rearrangement[J]. Tetrahedron, 2010, 66 27: Pages 5053-5058. DOI:
10.1016/j.tet.2010.04.134.
