Prostaglandins intermediates. Reduction of (E)-oxolactone by means of a chiral phase transfer catalyst.
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.
Passarotti
C
C
Formenti Group, Research Laboratories, Origgio (Va) Italy.
Bandi
G L
GL
Fossati
A
A
Valenti
M
M
Dal Bo
L
L
D001713:Biphenyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry*; D007783:Lactones; D009682:Magnetic Resonance Spectroscopy; D011465:Prostaglandins, Synthetic / Q000138:chemical synthesis* / Q000737:chemistry
D001713:Biphenyl Compounds; D003517:Cyclopentanes; D007783:Lactones; D011465:Prostaglandins, Synthetic; C068248:3A,4,5,6a-hexahydro-2-oxo-4-(3-oxo-5-(3-pyridyl)-1-pentenyl)-2H-cyclopenta(b)furan-5-yl(1,1'-biphenyl)-4-carboxylate