Directed Metalation Linked to Transition Metal Catalyzed Cascade Reactions: Two Total Syntheses of Plicadin, the Alleged Coumestan from Psoralea plicata

✍ Scribed by Brian A. Chauder; Alexey V. Kalinin; Nicholas J. Taylor; Victor Snieckus

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 107 KB
• Volume: 38
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/(sici)1521-3773(19990517)38:10<1435::aid-anie1435>3.0.co;2-b

✦ Synopsis

The oxygen-rich heterocyclic compound 1-which was proposed to be the structure of plicadin, the alleged naturally occurring coumestan from the herb Psoralea plicata-was synthesized by the rational combinations of directed ortho and remote metalation reactions with cascades of Negishi, Sonogashira, Castro-Stephens, and carbamoyl Baker-Venkataraman reactions.