Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2010 Jul 1;2010(11):1641-1646.
doi: 10.1055/s-0029-1220128.

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

Affiliations

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

David R Williams et al. Synlett. .

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.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3

References

    1. Taylor EC, Wipf P. Oxazoles: Synthesis, Reactions, And Spectrometry. John Wiley & Sons; Hoboken: 2003.
    1. For examples, see: Ichiba T, Yoshida WY, Scheuer PJ, Higa T, Gravalos DG. J Am Chem Soc. 1991;113:3173.Shin-ya K, Wierzba K, Matsuo K, Ohtani T, Yamada Y, Furihata K, Hayakawa Y, Seto H. J Am Chem Soc. 2001;123:1262.Searle PA, Molinski TF. J Am Chem Soc. 1995;117:8126.Rosener JA, Scheuer PJ. J Am Chem Soc. 1986;108:846.Dalisay DS, Rogers EW, Edison AS, Molinski TF. J Nat Prod. 2009;72:732.Li J, Burgett AWG, Esser L, Amezcua C, Harran PG. Angew Chem Int Ed. 2001;40:4770.Irschik H, Jansen R, Gerth K. J Antibiot. 1995;48:31.

    1. For examples, see: Kanoh K, Matsuo Y, Adachi K, Imagawa H, Nishizawa M, Shizuri Y. J Antibiot. 2005;58:289.Perez LJ, Faulkner DJ. J Nat Prod. 2003;66:247.Kohno J, Kameda N, Nisho M, Kinumaki A, Komatsubara S. J Antibiot. 1996;49:1063.

    1. Phillips AJ, Uto Y, Wipf P, Reno MJ, Williams DR. Org Lett. 2000;2:1165. - PubMed
    2. (b) For the initial application of this methodology in the synthesis of hennoxazole A, see: Williams DR, Brooks DA, Berliner MA. J Am Chem Soc. 1999;121:1303.Wipf P, Rahman LT, Rector SR. J Org Chem. 1998;63:7132.Wipf P, Miller CP. J Org Chem. 1993;58:3604.

    1. Besselièvre F, Piguel S, Mahuteau-Betzer F, Grierson DS. Org Lett. 2008;10:4029. - PubMed
    2. Flegeau EF, Popkin ME, Greaney MF. Org Lett. 2008;10:2717. - PubMed
    3. Hodgetts KJ, Kershaw MT. Org Lett. 2002;4:2905. - PubMed
    4. Smith AB, III, Minbiole KP, Freeze S. Synlett. 2001:1739.