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Research Article Open access CC BY 4.0

Total Syntheses of Chloropupukeananin and Its Related Natural Products

Takahiro Suzuki

Organics · pp. 304–319 · Published 9 Sep 2022

10.3390/org3030023

Abstract

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.

Natural product Biosynthesis Chemistry Total synthesis Stereochemistry Decane Organic chemistry Enzyme

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