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Award ID contains: 2154393

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  1. ; ; ; (, Angewandte Chemie International Edition)
    Abstract Pyritides belong to the ribosomally synthesized and post‐translationally modified peptide class of natural products that were recently genome‐predicted and are structurally defined by unique pyridine‐containing macrocycles. Inspired by their biosynthesis, proceeding through peptide modification and cycloaddition to form the heterocyclic core, we report the chemical synthesis of pyritide A2 involving pyridine ring synthesis from an amino acid precursor through aza‐Diels–Alder reaction. This strategy permitted the preparation of the decorated pyridine core with an appended amino acid residue in two steps from a commercially available arginine derivative and secured pyritide A2 in ten steps. Moreover, the synthetic logic enables efficient preparation of different pyridine subunits associated with pyritides, allowing rapid and convergent access to this new class of natural products and analogues thereof. 
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  2. ; ; ; ; (, Journal of the American Chemical Society)
    Concise total syntheses of several 5/7/6 norcembranoids, including ineleganolide, scabrolide B, sinuscalide C, and fragilolide A have been achieved through a fragment coupling/ring closure approach. The central seven-membered ring was forged through sequential Mukaiyama–Michael/aldol reactions using norcarvone and a decorated bicyclic lactone incorporating a latent electrophile. Subsequent manipulations installed the reactive enedione motif and delivered scabrolide B in 11 steps from a chiral pool-derived enone. Finally, ineleganolide, sinuscalide C, and fragilolide A were each accessed in one additional step. 
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    Free, publicly-accessible full text available January 8, 2026
  3. ; ; ; ; (, Journal of the American Chemical Society)
    The concise total syntheses of oxidized norcembranoid terpenoids (−)-scabrolide A and (−)-yonarolide have been accomplished in 10 and 11 steps, respectively. The carbocyclic skeleton was efficiently constructed from two chiral-pool-derived fragments, including a [5,5]-bicyclic lactone accessed through a powerful Ni-catalyzed pentannulation of functionalized cyclopentenone with methylenecyclopropane and subsequent fragmentation. Additional features included a Liebeskind–Srogl coupling, induction of a cyclization/elimination cascade by a zinc-amido base, and installation of a sensitive enedione motif by late-stage γ-oxidation. 
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  4. ; ; ; ; ; ; ; ; ; ; et al (, Journal of the American Chemical Society)
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