title: Efficient Suzuki and Stille Reactions for Regioselective Strategies of Incorporation of the 1,3-Oxazole Heterocycle. Mild Desulfonylation for the Synthesis of C-4 and C-5 Monosubstituted Oxazoles.
abstract: Suzuki and Stille cross-coupling reactions are surveyed for site-selective C-4 and C-5 elaboration of 2-(phenylsulfonyl)-1,3-oxazole derivatives. Conditions for mild reductive desulfonylations provide for direct incorporation of the intact oxazole heterocycle through bonding at C-4 and C-5.
authors.affiliation: Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, IN 47405-7102, USA.
authors.forename: David R
authors.initials: DR
authors.lastname: Williams
authors.forename: Liangfeng
authors.initials: L
authors.lastname: Fu
references.citation: J Antibiot (Tokyo). 1995 Jan;48(1):31-5
references.pmid: 7868386
references.citation: Org Lett. 2010 Feb 19;12(4):808-11
references.pmid: 20085311
references.citation: J Nat Prod. 2003 Feb;66(2):247-50
references.pmid: 12608858
references.citation: Synlett. 2009 Dec 22;2010(4):591-594
references.pmid: 20640045
references.citation: J Nat Prod. 2009 Apr;72(4):732-8
references.pmid: 19254038
references.citation: Org Lett. 2000 Apr 20;2(8):1165-8
references.pmid: 10804580
references.citation: J Antibiot (Tokyo). 2005 Apr;58(4):289-92
references.pmid: 15981418
references.citation: J Org Chem. 1998 Oct 16;63(21):7132-7133
references.pmid: 11672349
references.citation: J Antibiot (Tokyo). 1996 Oct;49(10):1063-5
references.pmid: 8968404
references.citation: Org Lett. 2002 Aug 22;4(17):2905-7
references.pmid: 12182585
references.citation: Org Lett. 2008 Jul 3;10(13):2717-20
references.pmid: 18540631
references.citation: J Am Chem Soc. 2001 Feb 14;123(6):1262-3
references.pmid: 11456694
references.citation: J Org Chem. 1998 Feb 6;63(3):551-555
references.pmid: 11672044
references.citation: Org Lett. 2008 Sep 18;10(18):4029-32
references.pmid: 18720988
references.citation: Angew Chem Int Ed Engl. 2001 Dec 17;40(24):4770-4773
references.pmid: 12404412
references.citation: Org Lett. 2009 Mar 19;11(6):1457-9
references.pmid: 19239243