Concise Total Synthesis of (+)-Lyconadin A
Concise Total Synthesis of (+)-Lyconadin A
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DOI：
10.1021/ja109516f
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发表时间：
2011-01-26
影响因子：
15
通讯作者：
Fukuyama, Tohru
中科院分区：
文献类型：
--
作者：
Nishimura, Takuya;Unni, Aditya K.;Fukuyama, Tohru
以（R）-5-甲基环己-2-烯酮为原料，全合成了石蒜素A。我们的合成特点是通过氮杂-普林斯反应和电环开环的组合，轻松构建高度稠合的四环化合物。四环素中溴代烯烃部分的转化可以通过乙烯基Pummerer重排或亚硝基烯烃的形成和随后的异构化来实现，以提供α，β-不饱和酮，吡啶酮环由其构成。
The total synthesis of lyconadin A from (R)-5-methylcyclohex-2-enone was accomplished. Our synthesis features the facile construction of a highly fused tetracyclic compound through a combination of an aza-Prins reaction and an electrocyclic ring opening. Transformation of the bromoalkene moiety in the tetracycle could be achieved by either a vinylogous Pummerer rearrangement or the formation and subsequent isomerization of the nitrosoalkene to furnish an alpha,beta-unsaturated ketone, from which the pyridone ring was constructed.