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Start Over Descriptor "Prostaglandins, Synthetic chemistry" Journal bollettino chimico farmaceutico

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1. Prostaglandins intermediates. Reduction of (E)-oxolactone by means of a chiral phase transfer catalyst.

Author

Passarotti C, Bandi GL, Fossati A, Valenti M, and Dal Bo L

Subjects
Catalysis, Magnetic Resonance Spectroscopy, Prostaglandins, Synthetic chemistry, Biphenyl Compounds chemistry, Cyclopentanes chemistry, Lactones, Prostaglandins, Synthetic chemical synthesis
Abstract

Preparation of (15 S)-hydroxy derivative (1-b), a key intermediate in the synthesis of PG like compounds, by reduction the corresponding enone (2), is described. High yields in (S)-isomer was obtained by means of chiral phase-transfer catalyst: (-)-N-(1-dodecyl)-N-methylephedrinium bromide. Eleven ammonium quaternary salts derived from (-)-N-methylephedrine were prepared and tested as catalyst in the reduction of enone (2) with NaBH4. Synthesis of enone (2), from phosphonate (6) (via Wadsworth-Emmons reaction) is also described.

Published
1990

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