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
- PMID: 20802797
- PMCID: PMC2927007
- 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
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.
References
-
- Taylor EC, Wipf P. Oxazoles: Synthesis, Reactions, And Spectrometry. John Wiley & Sons; Hoboken: 2003.
-
-
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.
-
-
-
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.
-
-
- Phillips AJ, Uto Y, Wipf P, Reno MJ, Williams DR. Org Lett. 2000;2:1165. - PubMed
-
(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.
Grants and funding
LinkOut - more resources
Full Text Sources
Molecular Biology Databases
Miscellaneous