A brief and efficient approach for the synthesis of (±)‐5‐benzyl‐4‐hydroxy‐2‐pyrrolidine (1) from phenylalanine racemate is described. The key step is the stereocontrolled reduction of the keto functionality of benzylated pyrrolidinone intermediate (6) via sodium borohydride in carboxylic acid medium furnishing both (R,R)‐ and (S,S)‐configured diastereomers. The natural (R,R) enantiomer (2), however, crystallized out from its racemic mixture. Structure of 2 was confirmed by NMR, IR, elemental analyzer, and single crystal X‐ray crystallographic techniques.

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A short synthesis of the natural (4R,5R)‐streptopyrrolidine (I) and its unnatural (4S,5S) enantiomer is described.

ChemInform Abstract Acid-catalyzed reaction of the 2-aroyl-3-nitrobenzoic acids (I) with polyhydroxyarenes such as (II) yields the analogs (III) of phthalein dyes. These are subjected to some modifications such as acetylation and bromination. Further examples are given in the original paper.