天然产物Luxenchalcone的全合成

Total Synthesis of Natural Product Luxenchalcone

以对羟基苯甲醛和2,4-二羟基苯乙酮为起始原料,经过甲氧甲基化、溴代、Ullmann反应、羟醛缩合和脱保护等反应,完成了天然产物双查尔酮Luxenchalcone的全合成,关键步骤为Ullmann反应,重要中间体和目标产物的化学结构经1H NMR,13C NMR和ESI-MS等表征确认.

Luxenchalcone was first isolated from the leaves of Luxemburgia octandra in 2004 by Brazil chemists. In 2007 this compound was proved to have significant cytotoxicity on HT-29 colon adenocarcinoma, NC1-H460 non-small cell lung carcinoma, MCF-7 breast cancer cell, OVCAR-3 ovarian adenocarcinoma cells and RXF-393 renal cell carcinoma. But the natural compound has not been synthesized in the literature. In order to synthesize Luxenchalcone, based on the natural product symmetry, the key step was Ullmann reac- tion, and then the natural product was easily to obtain by aldo condensation. In this work, Luxenchalcone was synthesized by methoxymethylation, bromination, Ullamnn reaction, aldo condenstion, deprotective group from 2,4-bihydroxyacetophone and 4-hydroxybenzaldehyde in 18% overyield. The structure of Luxenchalcone and intermediates were confirmed by 1H NMR, 13 C NMR and ESI-MS. The synthesis of this compound maybe gives some vital significance to find lead compounds.