Total Synthesis of Natural Product Luxenchalcone

doi:10.7503/cjcu20130306

Abstract

Abstract:

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, NCl-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 reaction, 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, ¹³C NMR and ESI-MS. The synthesis of this compound maybe gives some vital significance to find lead compounds.

Key words: Luxenchalcone, Ullmann reaction, Bichalcone, Total synthesis

CLC Number:

O625.1

TrendMD:

ZHANG Ying-Peng, ZHANG Wei-Na, YANG Yun-Shang, QIAO Ming. Total Synthesis of Natural Product Luxenchalcone[J]. Chem. J. Chinese Universities, 2013, 34(12): 2734.

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