Side-chain Modifications of Highly Functionalized 3(2H)-Furanones 英文参考文献.docVIP

Molecules 2012, 17, 12151-12162; doi:10.3390/molecules171012151 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Side-chain Modifications of Highly Functionalized 3(2H)-Furanones Viviani Nardini *, Shirley Muniz Machado Rodrigues, Maurício Gomes Constantino and Gil Valdo José da Silva Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeir?o Preto, Universidade de S?o Paulo, Avenida dos Bandeirantes, 3900, 14040-901 Ribeir?o Preto, SP, Brazil * Author to whom correspondence should be addressed; E-Mail: viviani@fcfrp.usp.br; Tel.: +55-16-3602-3879; Fax: +55-16-3633-8151. Received: 29 August 2012; in revised form: 14 September 2012 / Accepted: 7 October 2012 / Published: 16 October 2012 Abstract: A series of 3(2H)-furanones, based on side-chain modifications of a parent 3(2H)-furanone, was synthesized in good yield. The parent compound was prepared by hydrogenolysis, and subsequent acid hydrolysis, of isoxazole derivatives. The isoxazole was prepared by a [3+2] 1,3-dipolar cycloaddition reaction between 3-butyn-2-ol and nitrile oxide. Keywords: 3(2H)-furanone; isoxazole; natural products; side-chain modifications 1. Introduction As a prominent structural feature, 3(2H)-furanone seems to be relevant in many classes of biologically active natural products, such as the examples collected in Figure 1 [1–4]. Sesquiterpene lactones encompass a large class of natural products showing a large diversity of molecular structures and a variety of biological activities. For a long time, much attention has been given to the α-methylenelactone unit, as can be seen in the structure of goyazensolide, because this group is considered to be responsible for activities such as cytotoxicity [5,6], through a mechanism involving a Michael addition of a cysteine sulfhydryl group [7]. Later, it was shown that many sesquiterpene lactones lacking the