Palladium-Catalyzed Routes to Geranylated or Farnesylated Phenolic Stilbenes: Synthesis of Pawhuskin C and Schweinfurthin J

Abstract

Starting from double MOM-protected phloroglucinol, the facile total syntheses of bioactive natural products pawhuskin C and schweinfurthin J were accomplished in good overall yields. The Heck, Stille, or Suzuki coupling reactions of two different electron-rich phenolic segments bearing geranylated or farnesylated units were involved in the decisive step. The Sonogashira coupling reaction followed by palladium-catalyzed chemo- and stereoselective cis-reduction of an alkyne unit and subsequent isomerization to give the desired natural products is also described.

Key words

total synthesis - natural products - geranylated or farnesylated stilbenes - palladium-catalyzed coupling reactions - phloroglucinol

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