General Methodology for the Preparation of 2,5-Disubstituted-1,3-oxazoles
- 19 January 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (4), 808-811
- https://doi.org/10.1021/ol902833p
Abstract
Deprotonation of 2-(phenylsulfonyl)-1,3-oxazole (1) readily provides a useful C-5 carbanion that is reactive with a variety of electrophiles. Aldehydes and ketones are useful substrates, and the formation of 5-iodo- and 5-tri-n-butylstannyl oxazoles affords access to cross-coupling reactions. Subsequent nucleophilic displacement of the 2-phenylsulfonyl group provides a general route for the synthesis of 2,5-disubstituted-1,3-oxazoles.This publication has 30 references indexed in Scilit:
- Structure Elucidation at the Nanomole Scale. 1. Trisoxazole Macrolides and Thiazole-Containing Cyclic Peptides from the Nudibranch Hexabranchus sanguineusJournal of Natural Products, 2009
- The Absolute Configuration of Rhizopodin and Its Inhibition of Actin Polymerization by DimerizationAngewandte Chemie, 2008
- Mechercharmycins A and B, Cytotoxic Substances from Marine-derived Thermoactinomyces sp. YM3-251The Journal of Antibiotics, 2005
- Bistratamides E−J, Modified Cyclic Hexapeptides from the Philippines Ascidian Lissoclinum bistratumJournal of Natural Products, 2003
- Total Synthesis of Nominal Diazonamides-Part 2: On the True Structure and Origin of Natural IsolatesAngewandte Chemie, 2001
- Telomestatin, a Novel Telomerase Inhibitor from Streptomyces anulatusJournal of the American Chemical Society, 2001
- The Structures of Sulfomycins II and III.The Journal of Antibiotics, 1996
- Phorboxazoles A and B: potent cytostatic macrolides from marine sponge Phorbas speciesJournal of the American Chemical Society, 1995
- Hennoxazoles, bioactive bisoxazoles from a marine spongeJournal of the American Chemical Society, 1991
- Ulapualide A and B, extraordinary antitumor macrolides from nudibranch eggmassesJournal of the American Chemical Society, 1986