Divergent Total Syntheses of Hetero-Oligomeric Iridoid Glycosides
Divergent Total Syntheses of Hetero-Oligomeric Iridoid Glycosides
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DOI：
10.1021/acs.orglett.2c03965
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发表时间：
2023-01-06
期刊：
影响因子：
5.2
通讯作者：
Ishikawa，Hayato
中科院分区：
文献类型：
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作者：
Yoshidome，Akiho;Sakamoto，Jukiya;Ishikawa，Hayato
主要在川续断中发现的异源寡聚环烯醚萜苷类化合物得到了不同的全合成。因此，使用裂叶马钱素（2）作为底物，通过立体选择性还原环化有效地合成了作为单体单元重要的马钱素（1）。1和2的衍生物作为单体单元的顺序缩合反应导致杂寡聚体cantleyoside、（E）-aldosecologanin、dipsaperine、（3R，5S）-5-carboxyvincosidic acid 22-loganin ester和dipsanoside A的首次对映选择性全合成。
Divergent total syntheses of the hetero-oligomeric iridoid glycosides mainly found inDipsacus asperwere achieved. Thus, loganin (1), which is important as a monomer unit, was efficiently synthesized by stereoselective reductive cyclization using secologanin (2) as a substrate. Sequential condensation reactions of derivatives of1and2as monomer units led to the first enantioselective total syntheses of the heterooligomers cantleyoside, (E)-aldosecologanin, dipsaperine, (3R, 5S)-5-carboxyvincosidic acid 22-loganin ester, and dipsanoside A.