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Creators/Authors contains: "Okha, Fese M"

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  1. ; ; (, Organic Letters)
    ABSTRACT: Studies have described a highly convergent plan toward the synthesis of leiodolide A (1), a potent cytotoxic sponge metabolite. The enantiocontrolled preparation of aldehyde 6 is achieved with the application of several advances of methodology for the synthesis of substituted 1,3-oxazoles. Efforts have examined the halogen dance reaction, the selectivity of Stille cross coupling reactions of 4-bromo-1,3-oxazoles, and nucleophilic displacement of the 2-phenylsulfonyl substitu-ent with organolithium reagents as preparatively useful reactions. These techniques have facilitated the efficient synthesis of 6 from the starting bromide 12, alkenylstannane 16 and the primary nonracemic alcohol 25. 
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    Free, publicly-accessible full text available March 14, 2026
  2. ; ; (, Organic Letters)
    ABSTRACT: A convergent route toward the synthesis of leiodolide A (1) is described. Our studies explore reactions of the indium chloride-induced transmetallation of allylic stannane 32 for nucleophilic addition with nonracemic aldehyde 15. The stereoselective formation of the all-syn stereotriad was rationalized by in situ isomerization to produce the Z-allylindium reagent for subsequent anti-Felkin addition. The inversion of C17 stereochemistry led to an effective -allyl Stille cross cou-pling utilizing Z-alkenylstannane 11b. The Horner–Wadsworth–Emmons reaction provides macrolactone 37 which exhibits discrepancies as compared to reported NMR data for purported leiodolide A. 
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    Free, publicly-accessible full text available March 14, 2026