title: Approaches to N-methylwelwitindolinone C isothiocyanate: facile synthesis of the tetracyclic core.
abstract: The synthesis of a functionalized, tetracyclic core of N-methylwelwitindolinone C isothiocyanate is reported. The approach features a convergent coupling between an indole iminium ion and a highly functionalized vinylogous silyl ketene acetal followed by an intramolecular palladium-catalyzed cyclization that proceeds via an enolate arylation.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Richard W
authors.initials: RW
authors.lastname: Heidebrecht
authors.forename: Brian
authors.initials: B
authors.lastname: Gulledge
authors.forename: Stephen F
authors.initials: SF
authors.lastname: Martin
mesh_terms: D002384:Catalysis; D000458:Cyanobacteria / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D026121:Indole Alkaloids; C092268:N-methylwelwitindolinone C isothiocyanate
references.citation: Org Lett. 2009 Nov 19;11(22):5330-3
references.pmid: 19860385
references.citation: Tetrahedron Lett. 2009 Jul 1;50(26):3253-3257
references.pmid: 20161309
references.citation: Org Lett. 2000 May 18;2(10):1485-7
references.pmid: 10814479
references.citation: Org Lett. 2005 Sep 15;7(19):4087-9
references.pmid: 16146358
references.citation: Mol Pharmacol. 1995 Feb;47(2):241-7
references.pmid: 7870031
references.citation: Chem Pharm Bull (Tokyo). 1985 Jul;33(7):2890-5
references.pmid: 3841300
references.citation: J Am Chem Soc. 2002 Jun 5;124(22):6343-8
references.pmid: 12033863
references.citation: J Org Chem. 2008 Apr 4;73(7):2920-3
references.pmid: 18321122
references.citation: Org Lett. 2001 Sep 20;3(19):3001-4
references.pmid: 11554828
references.citation: J Am Chem Soc. 2008 Dec 31;130(52):17938-54
references.pmid: 19035635
references.citation: Org Lett. 2006 Nov 9;8(23):5287-9
references.pmid: 17078699
references.citation: Org Lett. 2005 Aug 4;7(16):3421-4
references.pmid: 16048307
references.citation: J Am Chem Soc. 2006 Feb 8;128(5):1448-9
references.pmid: 16448105
references.citation: Org Lett. 2009 Jun 4;11(11):2349-51
references.pmid: 19432408
references.citation: J Am Chem Soc. 2005 Nov 9;127(44):15394-6
references.pmid: 16262402
references.citation: Angew Chem Int Ed Engl. 2004 Feb 27;43(10):1270-2
references.pmid: 14991796
references.citation: Org Lett. 2009 Aug 20;11(16):3782-5
references.pmid: 19606876
references.citation: Org Lett. 2006 Jun 8;8(12):2643-5
references.pmid: 16737334
references.citation: J Am Chem Soc. 2008 Feb 13;130(6):2087-100
references.pmid: 18198870
references.citation: Chem Commun (Camb). 2009 Mar 21;(11):1398-400
references.pmid: 19259600