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An efficient total synthesis of the cytotoxic spiroketal natural products aculeatin A and B is described. The synthesis of the 1,3,5‐triol moiety with appropriate configuration was accomplished from the commercially available L‐malic acid. The key steps in this synthesis are the Barbier allylation, LiAlH4/LiI‐mediated syn‐stereoselective 1,3‐asymmetric reduction, and phenyliodine bis(trifluoroacetate) (=[bis(trifluoroacetoxy)iodo]benzene; PIFA) mediated oxidative spirocyclization.
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Yadav et al. (2010) studied this question.
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