ArticleJournal of the American Chemical Society2025
Total Synthesis and Anticancer Study of (+)-Verticillin A.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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5 authors.
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Abstract
We report the first total synthesis of (+)-verticillin A, over 50 years after the fungal metabolite was first isolated. Our initial strategy for sulfidation of a dimeric diketopiperazine (DKP) delivered the undesired stereochemistry for the epidithiodiketopiperazine (ETP) substructures of the alkaloid (+)-verticillin A. We later developed a protocol to directly introduce the disulfide with the correct relative stereochemistry on a complex DKP using benzhydryl hydrodisulfide prior to dimerization. Given the sensitivity of ETPs to carbon-centered radicals and UV irradiation, we developed a strategy to mask the disulfide as a pair of alkyl sulfides prior to an ambitious radical dimerization, fusing two bis-sulfide DKPs at the C3-C3' linkage, followed by photochemical N1 desulfonylation. A final-stage unveiling of the ETP substructures furnished (+)-verticillin A, the first dimeric ETP natural product containing C12 oxygenation to be accessed by total synthesis. (+)-Verticillin A and its
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