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Total Synthesis of (−)-Xestosaprol N and O
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-19 00:00:00 , DOI: 10.1021/acs.orglett.7b03865
Yingbo Shi 1 , Yang Ji 1 , Kunyun Xin 1 , Shuanhu Gao 1, 2
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The first total synthesis of (−)-xestosaprol N and O is described. This synthetic work features a convergent strategy: (1) a Pd-catalyzed arylation followed by cyclization to build a naphthalene fragment (ring C, D); (2) utilization of (−)-quinic acid to construct the chiral hydroxyl group at C-2; (3) a substrate controlled intramolecular Heck reaction to construct a quaternary carbon center (ring B); (4) introduction of a hypotaurine moiety at a late stage to furnish the E ring.

中文翻译:

(-)-Xestosaprol N和O的全合成

描述了(-)-xestosaprol N和O的第一个全合成。这项合成工作具有收敛策略的特点:(1)Pd催化的芳基化反应,然后环化生成萘片段(C,D环);(2)利用(-)-奎尼酸在C-2上构成手性羟基。(3)通过底物控制的分子内Heck反应来构建季碳中心(环B);(4)在后期引入亚牛磺酸部分以提供E环。
更新日期:2018-01-19
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