Abstract
An efficient three-step solid-phase synthesis of diverse 3,5-disubstituted-2-aminofuranones has been developed. α-Hydroxy acids loaded on a nitrophenyl carbonate derivative of Wang resin are used as acylating agents for the C-acylation of active methylene compounds and the resulting intermediates provided, through a cyclative cleavage reaction, the desired product.
Highlights
Multistep organic syntheses can be substantially facilitated by conducting reactions on substrates that are covalently attached to insoluble supports
Our group has paid particular attention to the synthesis of tetramic [22], tetronic [23] and thiotetronic acids [24], as well as other heterocycles which contain two points of diversity in solution and, recently, in solid phase synthesis via cyclization reactions of functionalized butenoates derived from active esters of α-amino acids and α-hydroxy acids [25]
We tried the synthesis of the polymer support from Wang resin because of the ease of preparation and the high cost of the commercial resin
Summary
Multistep organic syntheses can be substantially facilitated by conducting reactions on substrates that are covalently attached to insoluble supports. Our group has reported in a previous work the synthesis of many 2-aminofuranone derivatives in solution phase [21]. Our group has paid particular attention to the synthesis of tetramic [22], tetronic [23] and thiotetronic acids [24], as well as other heterocycles which contain two points of diversity in solution and, recently, in solid phase synthesis via cyclization reactions of functionalized butenoates derived from active esters of α-amino acids and α-hydroxy acids [25].
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
