Palladium-catalyzed routes to geranylated or farnesylated phenolic stilbenes: synthesis of pawhuskin C and schweinfurthin J

TitlePalladium-catalyzed routes to geranylated or farnesylated phenolic stilbenes: synthesis of pawhuskin C and schweinfurthin J
Publication TypeJournal Article
Year of Publication2012
AuthorsSingh, M, Argade, NP
JournalSynthesis-Stuttgart
Volume44
Issue18
Pagination2895-2902
Date PublishedSEP
ISSN0039-7881
Keywordsgeranylated or farnesylated stilbenes, Natural products, palladium-catalyzed coupling reactions, phloroglucinol, Total synthesis
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.

DOI10.1055/s-0032-1316765
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.5
Divison category: 
Organic Chemistry