Solid-Phase Synthesis of Optically Active Substituted 2 Aminofuranones Using an Activated Carbonate Linker 英文参考文献.docVIP

Molecules 2009, 14, 3914-3921; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Solid-Phase Synthesis of Optically Active Substituted 2-Aminofuranones Using an Activated Carbonate Linker Dimitris Matiadis, Kyriakos C. Prousis and Olga Igglessi-Markopoulou * Laboratory of Organic Chemistry, School of Chemical Engineering, National Technical University of Athens, Zografou Campus, Athens 15773, Greece * Author to whom correspondence should be addressed; E-Mail: ojmark@orfeas.chemeng.ntua.gr; Tel.: +30 210 772 3 079; Fax: +30 210 772 3 072. Received: 8 September 2009; in revised form: 29 September 2009 / Accepted: 30 September 2009 / Published: 30 September 2009 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. Keywords: 2-aminofuranones; solid-phase synthesis; heterocycles; lactones; acylations Introduction Multistep organic syntheses can be substantially facilitated by conducting reactions on substrates that are covalently attached to insoluble supports. The principles of “solid-phase synthesis” were introduced in 1963 by Merrifield [1]. Since then, the concept of solid phase synthesis has been applied extensively in numerous areas [2-5] such as peptides and oligonucleotides, and there has been significant progress in small molecules, especially heterocycles, due to several advantages over solution-phase methodologies. A crucial point in the design of compound libraries and, in particular, for cyclative cleavage strategies [6,7], is the careful choice of the appropriate linker unit. The li