Total Synthesis of (-)-Agelastatin A: The Application of a Sequential Sigmatropic Rearrangement

Total Synthesis of (-)-Agelastatin A: The Application of a Sequential Sigmatropic Rearrangement
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DOI:
10.1021/ol900799e
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发表时间:
2009-06-18
期刊:
影响因子:
5.2
通讯作者:
Chida, Noritaka
Chida, Noritaka
中科院分区:
化学1区
文献类型:
--
作者:
Hama, Naoto;Matsuda, Tomoki;Chida, Noritaka

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本文报道了以(-)-2,3-O-异亚丙基-D-苏糖醇为原料,对映选择性全合成(-)-agelastatin A的方法。烯丙基双三氯亚胺酯的顺序Overman/ Mislow-Evans重排是关键步骤,有效地安装了一个二氨基羟基。
An enantioselective total synthesis of (-)-agelastatin A from (-)-2,3-O-isopropylidene-D-threitol is described. The sequential Overman/ Mislow-Evans rearrangement of the allylic bistrichloroimidate is the key step, which efficiently installed a diaminohydroxy group.