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Creators/Authors contains: "Virgil, Scott C"

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  1. ; ; ; ; ; (, Chemical Science)
    Herein, we report a novel approach to pyrroloiminoquinones which was enabled by the development of a Larock/Buchwald–Hartwig annulation/cyclization cascade to rapidly construct the core, which was further elaborated to 5 of these natural products. 
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  2. ; ; ; ; ; ; ; ; ; ; et al (, Science)
    (−)-Cylindrocyclophane A is a 22-membered C2-symmetric [7.7]paracyclophane that bears bis-resorcinol functionality and six stereocenters. We report a synthetic strategy for (−)-cylindrocyclophane A that uses 10 C−H functionalization reactions, resulting in a streamlined route with high enantioselectivity and efficiency (17 steps). The use of chiral dirhodium tetracarboxylate catalysis enabled the C–H functionalization of primary and secondary positions, which was complemented by palladium-catalyzed C(sp2)–C(sp2) cross-couplings, resulting in the rapid formation of the macrocyclic core and all stereocenters with high regio-, diastereo-, and enantioselectivity. The use of a late-stage palladium-catalyzed fourfold C(sp2)–H acetoxylation installed the bis-resorcinol moieties. This research exemplifies how multilaboratory collaborations can produce substantial modernizations of complex total synthesis endeavors. 
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    Free, publicly-accessible full text available November 8, 2025
  3. ; ; ; ; ; (, Journal of the American Chemical Society)
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  4. ; ; ; ; ; (, Journal of the American Chemical Society)
  5. ; ; ; ; ; ; ; ; ; ; et al (, Science)
    The bis-tetrahydroisoquinoline (bis-THIQ) natural products have been studied intensively over the past four decades for their exceptionally potent anticancer activity, in addition to strong Gram-positive and Gram-negative antibiotic character. Synthetic strategies toward these complex polycyclic compounds have relied heavily on electrophilic aromatic chemistry, such as the Pictet–Spengler reaction, that mimics their biosynthetic pathways. Herein, we report an approach to two bis-THIQ natural products, jorunnamycin A and jorumycin, that instead harnesses the power of modern transition-metal catalysis for the three major bond-forming events and proceeds with high efficiency (15 and 16 steps, respectively). By breaking from biomimicry, this strategy allows for the preparation of a more diverse set of nonnatural analogs. 
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