We herein, report the first total synthesis of Dermacozine A and B in moderate to high yields from a commercially available methyl 2‐bromo (or chloro)‐3‐nitrobenzoate in an atom efficient route. The key carbon–nitrogen and carbon‐carbon bond forming reactions involve inter and intra‐molecular Pd (0) catalyzed N‐arylations and regioselective Friedel‐Crafts benzoylation respectively. Nitrile group was used as a masked carboxylic group to differentially functionalize two carboxylic acids to achieve Dermacozine C.
LTA reaction of homoallyl alcohols derived from norbornyl alpha-diketones exclusively furnished the corresponding alpha-diketones via beta-fragmentation of the allyl group in refluxing benzene while changing the solvent to MeOH resulted in the formation of novel methoxy substituted spirocyclic tetrahydrofuran products.
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