A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol
A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol
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DOI：
10.1021/jo034281f
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发表时间：
2003-08-08
影响因子：
3.6
通讯作者：
Lu, XY
中科院分区：
文献类型：
--
作者：
Du, YS;Lu, XY
在膦催化下，2，3-丁二烯酸叔丁酯或2-丁炔酸叔丁酯与3-甲基-2-亚甲基环己酮（5）发生[3+2]环加成反应，一步高立体选择性地构建了顺式香芹螺烷骨架。该方法的例证是首次高效全合成天然产物（-）-hinesol，其是脑循环和代谢改善剂的活性成分。
In one step, the skeleton of cis-spirovetivanes was constructed with high stereoselectivity by the phosphine-catalyzed [3+2] cycloaddition reaction of tert-butyl 2,3-butadienoate or 2-butynoate with 3-methyl-2-methylenecyclohexanone (5). This method was exemplified by the first highly efficient total synthesis of natural product (-)-hinesol, which is an active ingredient of cerebral circulation and metabolism improvers.