Asymmetric Total Synthesis of Dragonbloodins A1 and A2
Asymmetric Total Synthesis of Dragonbloodins A1 and A2
复制标题
Dragonbloodins A1 和 A2 的不对称全合成
DOI：
10.1021/acs.orglett.8b00315
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发表时间：
2018
期刊：
影响因子：
5.2
通讯作者：
Tang Yefeng
中科院分区：
文献类型：
--
作者：
Guo Zhen;Wang Zhiguo;Tang Yefeng
通过一系列合理设计或生物启发的转化，首次实现了龙血素A1和A2的不对称全合成。龙血素A1和A2是一对前所未有的查耳酮-黄烷杂三聚体。合成的关键要素包括高效的异源三聚反应，以在一锅中组装两个查耳酮单元和一个黄烷单元，以及串联的氧化脱芳构化/环化/氧化反应，以形成龙血素A1和A2的多环核心。本合成明确地证实了龙血素A1和A2的生物遗传关系和绝对立体化学。
The first asymmetric total synthesis of dragonbloodins A1 and A2, a pair of unprecedented chalcone-flavan heterotrimmers, has been achieved through a series of rationally designed or bioinspired transformations. Key elements of the synthesis include a highly efficient heterotrimerization reaction to assemble the two chalcone units and one flavan unit in one pot and a tandem oxidative dearomatization/cyclization/oxygenation reaction to forge the polycyclic core of dragonbloodins A1 and A2. The present synthesis unambiguously confirms the biogenetic relationship and absolute stereochemistry of dragonbloodins A1 and A2.