Practical Preparation of (3S)-Hydroxy-5-Phenylpentanoic Acid: Asymmetric Synthesis of (S)-Daphneolone and (S)-Dihydroyashabushiketol, and Formal Synthesis of (3S,5S)-Yashabushidiol B.

ABSTRACT: Many linear diarylpentanoids and diarylheptanoids contain a β-hydroxy ketone or 1,3-diol functionality as the structural motif. Reported herein is the asymmetric synthesis of (S)-daphneolone, (S)-dihydroyashabushiketol, and formal synthesis of (3S,5S)-yashabushidiol B as represented examples, employing readily accessible (3S)-hydroxy-5-phenylpentanoic acid. The (3S)-hydroxy-5-phenylpentanoic acid was conveniently prepared by the aldol addition of (R)-acetyloxazolidinone with 3-phenylpropanal affording two diastereomers which were cleanly separated by silica gel column chromatography, followed by the removal of Evans auxiliary of (3'R,4S)-imide. Then, the (S)-acid was converted to Weinreb amide as a privileged acylating a

SUBMITTER: Nam SY 

PROVIDER: S-EPMC11854942 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature