Differentiation of Nonconventional “Carbanions”—The Total Synthesis of Nemorosone and Clusianone

An unconventional approach: The total syntheses of nemorosone (1) and clusianone (2) have been achieved in a direct fashion through the generation and exploitation of nonconventional anions arising from a common intermediate (3, see scheme). The key skeleton-building stages are allylative de-aromatization and iodinative cyclization. These acylphloroglucinol natural products display promising cytotoxic and anti-HIV activity, respectively.