Total Syntheses of Chloropupukeananin and Its Related Natural Products by Takahiro Suzuki
Author:Takahiro Suzuki
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Tags: Chloropupukeananin is a natural product that inhibits HIV-1 replication and has antitumor activity. Its structure consists of a chlorinated tricyclo[4.3.1.03,7]decane core skeleton with an array of highly oxidized multifunctional groups. In the biosynthesis of chloropupukeananin, (+)-iso-A82775C and (-)-maldoxin are employed as biosynthetic precursors for the intermolecular Diels–Alder and carbonyl–ene reactions, followed by the migration of the p-orcellinate group. Chloropupukeanolides and chloropestolides are intermediates and isomers in biosynthesis; their unique chemical structures and biosynthetic pathways have attracted significant attention from synthetic chemists. In this review, I present the synthetic studies on chloropupukeananin and its related compounds that have been conducted thus far., biomimetic synthesis; Diels–Alder reactions; carbonyl–ene reactions; cascade reactions; enantioselective synthesis; natural products; total synthesis
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