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The Structural Revision and Total Synthesis of Carambolaflavone A
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-03-05 00:00:00 , DOI: 10.1021/acs.joc.8b00008 Yong Wang 1, 2 , Miao Liu 1 , Lei Liu 1 , Jian-Hui Xia 1 , Yu-Guo Du 2 , Jian-Song Sun 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-03-05 00:00:00 , DOI: 10.1021/acs.joc.8b00008 Yong Wang 1, 2 , Miao Liu 1 , Lei Liu 1 , Jian-Hui Xia 1 , Yu-Guo Du 2 , Jian-Song Sun 1
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The synthesis of both enantiomers of carambolaflavone A, the antidiabetic and flavonoid C-glycoside, was achieved for the first time via a 12-longest-linear-step with 16% (l-fucose) and 11% (d-fucose) overall yields. Through the synthetic investigation, the adverse effect of 4A MS in Suzuki C-glycosylation was disclosed, the mechanism of hydrogen-bonded-phenol involved Suzuki C-glycosylation was clarified, and the authentic structure of carambolaflavone A was also determined.
中文翻译：
杨桃黄酮A的结构修订及全合成
杨桃黄酮A的两种对映异构体，抗糖尿病药和类黄酮C-糖苷的合成首次通过12个最长的线性步骤完成，总收率为16％（l-岩藻糖）和11％（d-岩藻糖）。 。通过综合研究，揭示了4A MS对Suzuki C-糖基化的不利影响，阐明了氢键酚参与Suzuki C-糖基化的机理，并确定了杨桃黄酮A的真实结构。
更新日期：2018-03-05
中文翻译：
杨桃黄酮A的结构修订及全合成
杨桃黄酮A的两种对映异构体，抗糖尿病药和类黄酮C-糖苷的合成首次通过12个最长的线性步骤完成，总收率为16％（l-岩藻糖）和11％（d-岩藻糖）。 。通过综合研究，揭示了4A MS对Suzuki C-糖基化的不利影响，阐明了氢键酚参与Suzuki C-糖基化的机理，并确定了杨桃黄酮A的真实结构。
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