Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD-594
Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD-594
复制标题
复杂多环呫吨酮FD-594的不对称全合成
DOI：
10.1002/anie.201915787
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Gao Shuanhu
中科院分区：
文献类型：
--
作者：
Xie Tao;Zheng Chaoying;Chen Kuanwei;He Haibing;Gao Shuanhu
开发了一种高度收敛的方法，以20步的最长线性序列（LLS）实现了FD-594的首次不对称和可扩展的全合成，FD-594是一种来自链霉菌TA-0256的复杂多环口山酮天然产物。反式-9，10-二氢菲-9，10-二醇片段（B-C-D环）是通过一种新的策略产生的，该策略涉及不对称二羟基化，然后是Cu介导的氧化环化。晚期立体选择性糖基化将角形六环框架与β连接的2，6-二脱氧三糖片段组装在一起。
A highly convergent approach was developed to achieve the first asymmetric and scalable total synthesis of FD‐594, a complex polycyclic xanthone natural product fromStreptomyces sp. TA‐0256, in a longest linear sequence (LLS) of 20 steps. Thetrans‐9,10‐dihydrophenanthrene‐9,10‐diol fragment (B‐C‐D ring) was generated through a new strategy involving asymmetric dihydroxylation followed by Cu‐mediated oxidative cyclization. Late‐stage stereoselective glycosylation assembled the angular hexacyclic framework with a β‐linked 2,6‐dideoxy trisaccharide fragment.