1369969-32-3Relevant articles and documents
Silver-promoted Friedel-Crafts reaction: Concise total synthesis of (-)-ardeemin, (-)-acetylardeemin and (-)-formylardeemin
Wang,Kong,Du,Song,Zhang,Qin
supporting information, p. 2793 - 2797 (2012/11/13)
Total syntheses of multidrug resistant inhibitors (-)-acetylardeemin 2a, (-)-ardeemin 2b, and (-)-formylardeemin 3 have been achieved within 10 steps starting from bromopyrroloinoline 13. The key step involves direct alkylation of 13 with prenyl tributylstannane 11 to yield 12via a silver-promoted asymmetric Friedel-Crafts reaction. Highly efficient installation of the isoprenyl group allowed excellent overall yield. Moreover, the substrate scope of the asymmetric Friedel-Crafts reaction of 13 was expanded to include a variety of arenes 14 to afford natural product-like library analogues 15. The Royal Society of Chemistry 2012.