Enantioselective Total Synthesis of (-)-Spiroxins A, C, and D
Enantioselective Total Synthesis of (-)-Spiroxins A, C, and D
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(-)-螺环素 A、C 和 D 的对映选择性全合成
DOI：
10.1002/anie.202105921
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Hu Xiangdong
中科院分区：
文献类型：
--
作者：
Shu Xin;Chen Chong-Chong;Yu Tao;Yang Jiayi;Hu Xiangdong
螺旋毒素A、C和D是在海洋真菌菌株LL‐37H248中发现的代谢物。它们独特的多环结构和有趣的生物活性使它们成为合成界的有吸引力的目标。基于5 -取代萘醌的可扩展的对映选择性环氧化反应、氧化/螺酮化级联反应、苯酚单元的邻位选择性氯化反应和肟酯定向乙酰化反应，已经实现了(−)-螺毒素a和C的对映选择性全合成，以及(−)-螺毒素D的首次全合成。
Spiroxins A, C, and D are metabolites that have been identified in the marine fungal strain LL‐37H248. Their unique polycyclic structures and intriguing biological activities make them attractive targets for the synthetic community. Based on a scalable enantioselective epoxidation of 5‐substituted naphthoquinone, an oxidation/spiroketalization cascade,ortho‐selective chlorination of the phenol unit, and oxime‐ester‐directed acetoxylation, an enantioselective total synthesis of (−)‐spiroxins A and C and the first total synthesis of (−)‐spiroxin D have been achieved.