title: Carbophilic 3-component cascades: access to complex bioactive cyclopropyl diindolylmethanes.
abstract: Naturally occurring indole-3-carbinol and 3,3-diindolylmethane show bioactivity in a number of disparate disease areas, including cancer, prompting substantial synthetic analogue activity. We describe a new approach to highly functionalised derivatives that starts from allene gas and proceeds via the combination of a three-component Pd(0)-catalysed cascade with a one-pot, three-component carbophilic Pt(II) cascade linked to a stereoselective acid-catalysed Mannich-Michael reaction that generates complex cyclopropyl diindolylmethanes which show selective activity against prostate cancer cell lines.
authors.affiliation: School of Chemistry, University of Leeds, Leeds, LS2 9 JT, UK.
authors.forename: Nigel M
authors.initials: NM
authors.lastname: Groome
authors.forename: Elghareeb E
authors.initials: EE
authors.lastname: Elboray
authors.forename: Martyn W
authors.initials: MW
authors.lastname: Inman
authors.forename: H Ali
authors.initials: HA
authors.lastname: Dondas
authors.forename: Roger M
authors.initials: RM
authors.lastname: Phillips
authors.forename: Colin
authors.initials: C
authors.lastname: Kilner
authors.forename: Ronald
authors.initials: R
authors.lastname: Grigg
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D002384:Catalysis; D002460:Cell Line / Q000737:chemistry* / Q000187:drug effects*; D003521:Cyclopropanes / Q000737:chemistry*; D006801:Humans; D007211:Indoles / Q000737:chemistry* / Q000494:pharmacology*; D008297:Male; D010165:Palladium / Q000737:chemistry*; D011471:Prostatic Neoplasms / Q000737:chemistry* / Q000188:drug therapy*; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D003521:Cyclopropanes; D007211:Indoles; D010165:Palladium; C016517:indole-3-carbinol; C016392:3,3'-diindolylmethane