Phosphoric Acid Catalyzed Desymmetrization of Bicyclic Bislactones Bearing an All-Carbon Stereogenic Center: Total Syntheses of (-)-Rhazinilam and (-)-Leucomidine B
Phosphoric Acid Catalyzed Desymmetrization of Bicyclic Bislactones Bearing an All-Carbon Stereogenic Center: Total Syntheses of (-)-Rhazinilam and (-)-Leucomidine B
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DOI：
10.1002/anie.201405842
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发表时间：
2014-09-08
影响因子：
16.6
通讯作者：
Zhu, Jieping
中科院分区：
文献类型：
--
作者：
Gualtierotti, Jean-Baptiste;Pasche, Delphine;Zhu, Jieping
在催化量的亚胺二磷酸存在下，双环双内酯与醇反应顺利地进行了对映选择性去对称化反应，得到了具有全碳立体生成中心的富含对映体的一元酸。以(S)-4-乙基-4-甲酰基戊二酸甲酯为起始原料，合成了(-)-雷奇尼仑和(-)-亮亮氨酸B。
In the presence of a catalytic amount of an imidodiphosphoric acid, enantioselective desymmetrization of bicyclic bislactones by reaction with alcohols took place smoothly to afford enantiomerically enriched monoacids having an all-carbon stereogenic center. Concise catalytic enantioselective syntheses of both (-)-rhazinilam and (-)-leucomidineB were subsequently developed using (S)-methyl 4-ethyl-4-formylpimelate monoacid as a common starting material.