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The importance of molecular diversity has been clearly recognized to identify specific bioactive small molecules for the elucidation of mysterious biological processes.The diversity-oriented synthesis (DOS) was introduced for efficient population of molecular diversity in untapped chemical space using complexity-generating synthetic route.To maximize the molecular diversity with high relevance in biological space,we pursued privilegedsubstructure-based DOS (pDOS) strategy to emphasize the importance of maximized skeletal diversity through the creative reconstruction of core skeletons containing privileged substructures.