Prostaglandins intermediates. Reduction of (E) -oxolactone by means of a chiral phase transfer catalyst
Passarotti, C.; Bandi, G.L.; Fossati, A.; Valenti, M.; Dal Bo, L.
Bollettino Chimico Farmaceutico 129(5): 195-198
1990
ISSN/ISBN: 0006-6648 PMID: 2083055 Document Number: 353503
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.