Pharmaceutically attractive methylene
lactone- and methylene lactam-based
spiro compounds have been synthesized by employing amido-functionalized
γ-hydroxylactam as a common intermediate. Development of a new
route for bifurcated synthesis of two types of N,O-spiro compounds was accomplished by treatment of the intermediate
under acidic conditions, leading to potent cytotoxic methylene lactone-based
spiro compounds. New methylene lactam-based N,N-spiro compounds could be delivered via N-tert-butyloxycarbonyl protection of the terminal
amide moiety of the intermediate followed by lactam cyclization under
basic conditions.
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