title: Silver-promoted Friedel-Crafts reaction: concise total synthesis of (-)-ardeemin, (-)-acetylardeemin and (-)-formylardeemin.
abstract: 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 12 via 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.
authors.affiliation: Key Laboratory of Drug Targeting of Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, PR China.
authors.forename: Y
authors.initials: Y
authors.lastname: Wang
authors.forename: C
authors.initials: C
authors.lastname: Kong
authors.forename: Y
authors.initials: Y
authors.lastname: Du
authors.forename: H
authors.initials: H
authors.lastname: Song
authors.forename: D
authors.initials: D
authors.lastname: Zhang
authors.forename: Y
authors.initials: Y
authors.lastname: Qin
mesh_terms: D026121:Indole Alkaloids / Q000138:chemical synthesis*; D015394:Molecular Structure; D012834:Silver / Q000737:chemistry*
chemical_list: D026121:Indole Alkaloids; C573950:acetylardeemin; C534892:ardeemin; C573951:formylardeemin; D012834:Silver