title: Annulated diketopiperazines from dipeptides or Schöllkopf reagents via tandem cyclization-intramolecular N-arylation.
abstract: Facile CuI-mediated N-arylation of diketopiperazine using the Fukuyama modification of the Ullmann-Goldberg reaction can be exploited in new approaches to enantiopure polycyclic diketopiperazines from easily assembled dipeptides or functionalized Schöllkopf reagents.
authors.affiliation: Department of Chemistry, The Ohio State University, 100 W. 18th Avenue, Columbus, Ohio 43210, USA.
authors.forename: Hwan Jung
authors.initials: HJ
authors.lastname: Lim
authors.forename: Judith C
authors.initials: JC
authors.lastname: Gallucci
authors.forename: T V
authors.initials: TV
authors.lastname: RajanBabu
mesh_terms: D003500:Cyclization; D054659:Diketopiperazines / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D008958:Models, Molecular
chemical_list: D054659:Diketopiperazines; D004151:Dipeptides; D007202:Indicators and Reagents
references.citation: J Med Chem. 1991 Aug;34(8):2420-30
references.pmid: 1875340
references.citation: Angew Chem Int Ed Engl. 1998 Aug 17;37(15):2046-2067
references.pmid: 29711045
references.citation: Org Lett. 2008 Sep 4;10(17):3841-4
references.pmid: 18681449
references.citation: Bioorg Med Chem Lett. 2003 Nov 3;13(21):3661-3
references.pmid: 14552752
references.citation: J Am Chem Soc. 2008 Jul 30;130(30):9971-83
references.pmid: 18597458
references.citation: Acc Chem Res. 2008 Nov 18;41(11):1450-60
references.pmid: 18698852
references.citation: Bioorg Med Chem Lett. 2007 Feb 1;17(3):789-92
references.pmid: 17107795
references.citation: J Am Chem Soc. 2006 Jun 7;128(22):7136-7
references.pmid: 16734447
references.citation: Chemistry. 2000 Jun 16;6(12):2160-7
references.pmid: 10926221
references.citation: Acc Chem Res. 2008 Nov 18;41(11):1534-44
references.pmid: 18681463
references.citation: J Am Chem Soc. 2004 Sep 22;126(37):11432-3
references.pmid: 15366877
references.citation: Chem Rev. 2008 Aug;108(8):3054-131
references.pmid: 18698737
references.citation: Org Lett. 2000 Dec 28;2(26):4137-40
references.pmid: 11150183
references.citation: Angew Chem Int Ed Engl. 2003 Nov 17;42(44):5400-49
references.pmid: 14618572
references.citation: J Org Chem. 2003 Dec 12;68(25):9835-8
references.pmid: 14656119
references.citation: J Am Chem Soc. 2003 Jun 4;125(22):6630-1
references.pmid: 12769562
references.citation: J Am Chem Soc. 2002 Jun 26;124(25):7421-8
references.pmid: 12071751
references.citation: Chem Rev. 2002 May;102(5):1359-470
references.pmid: 11996540