ChemInform Abstract: Palladium-Catalyzed Intramolecular Alkyne-α,β-Unsaturated Carbonyl Coupling. A Formal Synthesis of (+)-Pilocarpine.

✍ Scribed by Z. WANG; X. LU

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199743118

✦ Synopsis

Palladium-Catalyzed Intramolecular Alkyne-α,β-Unsaturated Carbonyl Coupling.

A Formal Synthesis of (+)-Pilocarpine.

-Pd-catalyzed enyne coupling of (E) or (Z) alkynoates (I) or (III) provides the alkenyl substituted lactones (II) highly stereoselectively. After esterification with (+)-dimethyltartrate and following chromatographic separation, the pure diastereomer (IV) is converted to aldehyde (VI), a known precursor of (+)-pilocarpine. -(WANG, Z.;