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Solid-phase synthesis of an isoxazolinopyrrole library.
Sung Hee Hwang1, Marilyn M Olmstead, Mark J Kurth
1Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616-5295, USA.
Journal of Combinatorial Chemistry
|January 13, 2004
Summary
A novel four-step solid-phase synthesis yields isoxazolinopyrroles using an acid-labile resin. This method efficiently produces valuable heterocyclic compounds from readily available starting materials.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Solid-phase synthesis offers advantages in purification and automation for complex molecule construction.
- Isoxazolinopyrroles are a class of heterocyclic compounds with potential biological activities.
Purpose of the Study:
- To develop an efficient four-step solid-phase synthesis for isoxazolinopyrroles.
- To utilize an acid-labile resin for facile cleavage of the final product.
Main Methods:
- The synthesis employed a 2-(4-formyl-3-methoxyphenoxy)ethyl polystyrene HL resin.
- Resin-bound vinyl sulfone was prepared via DIC coupling and solution-phase nitrile oxide cycloaddition.
- Pyrrole annulation on solid phase involved isocyano derivatives and potassium t-butoxide, followed by intramolecular condensation and hydrogen shift.
Main Results:
- The four-step solid-phase synthesis successfully generated isoxazolinopyrroles.
- The target compounds were cleaved from the resin using 10% trifluoroacetic acid (TFA).
- Moderate to excellent overall yields were achieved for the synthesized isoxazolinopyrroles.
Conclusions:
- A robust and efficient solid-phase strategy for isoxazolinopyrrole synthesis has been established.
- The use of an acid-labile resin facilitates product isolation and purification.
- This methodology provides a valuable route to substituted isoxazolinopyrroles.