Studies Toward the Total Synthesis of Schinortriterpenoids: Diastereoselective Synthesis of the Left‐Hand Fragment
Studies Toward the Total Synthesis of Schinortriterpenoids: Diastereoselective Synthesis of the Left‐Hand Fragment
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DOI：
10.1002/ejoc.202100510
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发表时间：
2021-05
影响因子：
2.8
通讯作者：
Ryotaro Yagita;K. Irie;C. Tsukano
中科院分区：
文献类型：
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作者：
Ryotaro Yagita;K. Irie;C. Tsukano
Schinortriperenoids，如pre-schisanartanin A和五味子内酯C，是复杂的和高度氧化的多环萜烯。在这项研究中，这类萜烯的左手片段，它具有在C19的氧官能度，通过[3+2]环加成合成具有良好的非对映选择性。这种立体选择性进行了研究，通过计算研究。进一步的选择性转化提供了具有所需立体化学的三环骨架。
Schinortriterpenoids, such as pre‐schisanartanin A and arisanlactone C, are complex and highly oxygenated polycyclic terpenes. In this study, the left‐hand fragment of this class terpenes, which possesses oxygen‐functionality at C19, was synthesized through [3+2] cycloaddition with excellent diastereoselectivity. This stereoselectivity was investigated by computational studies. Further selective transformation provided a tricyclic skeleton with the desired stereochemistry.