High diastereoselection in the aldol reaction of the bistrimethylsilyl enol ether of methyl acetoacetate with 2-benzyloxyhexanal: synthesis of (–)-pestalotin

Abstract
Aldol condensation of the bistrimethylsilyl enol ether of methyl acetoacetate, compound 2, with 2-benzyloxyhexanal 3c affords highly selectively (99:1) the syn-aldol adduct 4c in the presence of titanium tetrachloride. The stereocontrolled synthesis of (–)-pestalotin 7 has been achieved.

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