General method of synthesis for natural long-chain beta-diketones.
General method of synthesis for natural long-chain beta-diketones.
复制标题
天然长链β-二酮的一般合成方法。
DOI：
10.1021/np50052a012
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发表时间：
1987
影响因子：
5.1
通讯作者：
Hudlicky,T
中科院分区：
文献类型：
--
作者：
Barbieri,G;Seoane,G;Trabazo,JL;Riva,A;Umpierrez,F;Radesca,L;Tubio,R;Kwart,LD;Hudlicky,T
两种合成长链ß-二酮的一般方法已经被开发出来。第一种方法依赖于脂肪酸衍生的酸氯化物的丙二酸型烷基化，而第二种方法更直接，涉及与脂肪酸的酸氯化物偶联并随后水解长链乙炔。ß-具有31个碳原子的二酮和沿这条链自由分布的二酮部分是许多植物蜡中普遍存在的成分（1-7）。2这些化合物的衍生物如羟基酮或二醇也存在于许多物种中（2,4）。已经有人提出，这些化合物在保护草和叶子方面起着重要作用（1,3）。农业部门对这些化合物的兴趣促使我们研究了一种合成结构的一般方法1。由于脂肪酸的可用性和低成本，我们设计的任何ß-二酮都源于脂肪酸本身或从脂肪酸中容易获得的化合物。我们着手制备天然产物la和Id以及化合物lb和lc，预计它们的生物学性质可能相似。
Two general methods of synthesis have been developed for the preparation of long-chain ß-diketones. The first relies on malonate-type alkylationof acid chlorides derived from fatty acids, while the second, more direct method, involves coupling and subsequent hydrolysis of long-chain acetylenes with acid chlorides of fatty acids. ß-Diketones with 31 carbon atoms and the diketone moiety disposed freely along this chain are ubiquitous components of many plant waxes (1-7). 2 Derivatives of these compounds such as hydroxyketones or diols also exist in many species (2, 4). Sugges-tions that such compounds play an important role in the protection of grasses and leaves have been made (1, 3)· The interest of the agricultural sector in these compounds prompted us to investigate a general synthetic approach to structures 1. Because of the availability and the low cost of fatty acids our design for any of the ß-diketones origi-nated with either fatty acids themselves or compounds readily available from them. We set out to prepare especially the natural products la and Id and also compounds lb and lc, anticipating that their biological propertiesmay be similar.