Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols

Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols has been established starting from 2-benzyloxymethylpyrrolidin-2-one framework, which is derived from commercially available trans-(2S,4R)-4-hydroxyproline. The single diastereomer having a trans–cis relative configuration with C2 and C3 and C3 and C4 is constructed in two one-pot functional group transformations of Grignard addition/dehydration and epoxidation/isomerization as the key steps in moderate yield.

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