New total synthesis of the marine antitumor alkaloid (-)-agelastatin A
New total synthesis of the marine antitumor alkaloid (-)-agelastatin A
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DOI：
10.1021/ol0490476
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发表时间：
2004-07-22
期刊：
影响因子：
5.2
通讯作者：
Hale, KJ
中科院分区：
文献类型：
--
作者：
Domostoj, MM;Irving, E;Hale, KJ
以手性恶唑烷酮（-）-3为起始原料，实现了（-）-agelastatin A（1）的全合成。虽然烯酮转座是有问题的，当迈克尔环关闭2试图与强碱，所需的环化可以实现与Hunig碱后，吡咯核溴化。随后还原和单溴化得到合成的（-）-agelastatin A（1）。
A new total synthesis of (-)-agelastatin A (1) has been achieved from the chiral oxazolidinone (-)-3. Although enone transposition was problematic when the Michael ring closure of 2 was attempted with strong base, the desired cyclization could be effected with Hunig's base after the pyrrole nucleus was brominated. Subsequent reduction and monobromination afforded synthetic (-)-agelastatin A (1).