Intramolecular cyclobutadiene cycloaddition/cyclopropanation/thermal rearrangement: an effective strategy for the asymmetric syntheses of pleocarpenene and pleocarpenone.
Intramolecular cyclobutadiene cycloaddition/cyclopropanation/thermal rearrangement: an effective strategy for the asymmetric syntheses of pleocarpenene and pleocarpenone.
复制标题
分子内环丁二烯环加成/环丙烷化/热重排：多卡尔烯和多卡尔烯酮不对称合成的有效策略。
DOI：
10.1021/ja0674340
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发表时间：
2007
影响因子：
15
通讯作者：
Snapper,MarcL
中科院分区：
文献类型：
--
作者：
Williams,MichaelJ;Deak,HollyL;Snapper,MarcL
首次全合成了愈创木烷型倍半萜类天然产物多卡文酮和多卡文烯。环丁二烯的分子内环加成，然后环丙烷化和所得高度紧张的中间体的热断裂，是用于实现这种合成的策略。不对称路线允许确认这些天然产物的绝对立体化学。
The first total synthesis of the guaiane sesquiterpene natural products pleocarpenone and pleocarpenene is described. An intramolecular cycloaddition of cyclobutadiene, followed by cyclopropanation and thermal fragmentation of the resulting highly strained intermediate, is the strategy used to achieve this synthesis. The asymmetric route allowed for confirmation of the absolute stereochemistry of these natural products.