title: Directed oxidative cyclizations to C2- or C4-positions of indole: efficient construction of the bicyclo[4.3.1]decane core of welwitindolinones.
abstract: Regiocontrolled oxidative cyclizations of 3-substituted indoles are described herein. Specifically, it is shown that the installation of a chloride at C2 alters the inherent propensity for cyclization at the 2-position of indole so as to favor the 4-position, enabling the construction of the unique framework found in most welwitindolinone alkaloids. The chloride functions here as more than a blocking group, as it also provides ready access to the corresponding oxindole.
authors: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
authors: Vikram
authors: V
authors: Bhat
authors: James A
authors: JA
authors: Mackay
authors: Viresh H
authors: VH
authors: Rawal
references: Org Biomol Chem. 2010 Oct 21;8(20):4521-3
references: 20717611
references: Org Lett. 2008 Apr 3;10(7):1437-40
references: 18335949
references: Tetrahedron. 2010 Aug 14;66(33):6647-6655
references: 20733933
references: Chem Rev. 1996 Feb 1;96(1):339-364
references: 11848756
references: Org Lett. 2005 Sep 15;7(19):4087-9
references: 16146358
references: Org Lett. 2010 Jan 15;12(2):368-71
references: 20014770
references: Chem Commun (Camb). 2010 Nov 28;46(44):8436-8
references: 20886152
references: J Nat Prod. 1999 Apr;62(4):569-72
references: 10217710
references: J Org Chem. 2007 Aug 31;72(18):6885-90
references: 17685656
references: Chem Commun (Camb). 2009 Mar 21;(11):1398-400
references: 19259600
references: Org Lett. 2001 Sep 20;3(19):3001-4
references: 11554828
references: J Am Chem Soc. 2008 Dec 31;130(52):17938-54
references: 19035635
references: Org Lett. 2009 Nov 19;11(22):5330-3
references: 19860385
references: Org Lett. 2006 Sep 28;8(20):4561-4
references: 16986950
references: Org Lett. 2005 Aug 4;7(16):3421-4
references: 16048307
references: Org Biomol Chem. 2003 Jan 21;1(2):391-4
references: 12929435
references: Org Lett. 2009 Nov 5;11(21):4774-6
references: 19795876
references: Org Lett. 2009 Jun 4;11(11):2349-51
references: 19432408
references: Angew Chem Int Ed Engl. 2000 Feb;39(4):731-733
references: 10760851
references: J Am Chem Soc. 2011 Apr 20;133(15):5798-801
references: 21446729
references: Angew Chem Int Ed Engl. 2004 Feb 27;43(10):1270-2
references: 14991796
references: Org Lett. 2009 Aug 20;11(16):3782-5
references: 19606876
references: Org Lett. 2006 Jun 8;8(12):2643-5
references: 16737334
references: J Org Chem. 2000 Mar 10;65(5):1353-8
references: 10814096
references: Org Lett. 2010 Jun 4;12(11):2492-5
references: 20446675
references: Org Lett. 2006 Nov 9;8(23):5287-9
references: 17078699
references: Org Lett. 2007 Aug 16;9(17):3331-4
references: 17655251