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A Formal Synthesis of (-)-Paroxetine (I) by Enantioselective Ring Enlargement of a Trisubstituted Prolinol.

✍ Scribed by Janine Cossy; Olivier Mirguet; Domingo Gomez Pardo; Jean-Roger Desmurs


Publisher
John Wiley and Sons
Year
2003
Weight
59 KB
Volume
34
Category
Article
ISSN
0931-7597

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πŸ“œ SIMILAR VOLUMES


A Formal Synthesis of (βˆ’)-Paroxetine by
✍ Janine Cossy; Olivier Mirguet; DomingoΒ Gomez Pardo; Jean-Roger Desmurs πŸ“‚ Article πŸ“… 2002 πŸ› John Wiley and Sons 🌐 English βš– 184 KB

A ring expansion and a radical dehalogenation have been used as the key steps in a formal total synthesis of (-)-paroxetine. The substituted piperidine ring precursor of (-)-paroxetine was generated by means of a stereoselective ring expansion of prolinol.

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Bicyclo[n.1.0]alkylidene derivatives (ring-fused alkylidenecyclopropanes) reacted with diazomethane to give spiro-pyrazolines regioselectively. Thermal decomposition of spiro-pyrazolines resulted in ring-enlargement and afforded ring-fused alkylidenecyclobutanes (bicyclo[n.2.0]alkylidene derivatives