A new methodology is presented to synthesize in a regio and stereoselective manner tetrahydrofuro[3,2-b]furan-2(3H)-one, structural subunit present in a wide variety of natural products present in plant, fungi, algae, insects, and other living organisms. This secondary metabolites have important biological properties and have shown to be very active in different therapeutic areas. This method consists in the reaction of highly substituted 2-oxyallyl cations, generated in situ from the corresponding dihaloketone, and 2-functionalized furans (in our case 2-NHBoc-furan). It is a one-pot reaction that affords the desired furofuranones with high regio- and stereoselectivity. The new synthetic method is simple, straightforward and versatile, because a wide variety of furofuranones, and with wide molecular diversity, may be prepared by adequately designing the substituents of starting materials. The resulting furofuranones may be potentially derivatized to generate chemical libraries of high molecular diversity, which are very useful when developing structure–activity relationship studies.

中文翻译：

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合成四氢呋喃[3,2-b]呋喃-2（3H）-one衍生物，具有生物学兴趣的天然产物合成子的新方法

提出了一种新方法以区域和立体选择性方式合成四氢呋喃[3,2-b]呋喃-2（3H）-一种存在于植物，真菌，藻类，昆虫，和其他生物。这种次生代谢产物具有重要的生物学特性，并且在不同的治疗领域显示出非常高的活性。该方法包括由相应的二卤代酮原位生成的高度取代的2-氧基烯丙基阳离子与2-官能化的呋喃（在我们的情况下为2-NHBoc-呋喃）反应。这是一种一锅反应，可提供所需的呋喃并呋喃酮，具有较高的区域选择性和立体选择性。这种新的合成方法简单，直接且用途广泛，因为种类繁多的呋喃呋喃酮具有广泛的分子多样性，可以通过适当地设计原料的取代基来制备。由此产生的呋喃呋喃酮可能被衍生化以生成具有高分子多样性的化学文库，这在开展结构与活性关系研究时非常有用。