Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer

• DOI: 10.1016/j.tet.2011.06.054
• Publication Date: 2011-06-28T18:07:19Z
• Authors: Shankar Thangaraj; Wen-Shing Tsao; Yi-Wei Luo; Yean-Jang Lee; Chia-Fu Chang; Chun-Cheng Lin; Biing-Jiun Uang; Chia-Chun Yu; Jih-Hwa Guh; Che-Ming Teng
• Keywords: 01 natural sciences; 0104 chemical sciences; 3. Good health

Abstract The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC50 values of 0.7, 1.6, 2.5, and 1.5 μM, respectively.