Synthesis of tri-, tetra-, and pentacarbonyl derivatives via ozonolysis of 1,4-dienes and cyclization to polyaromatic systems.
Synthesis of tri-, tetra-, and pentacarbonyl derivatives via ozonolysis of 1,4-dienes and cyclization to polyaromatic systems.
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DOI：
10.1021/jo502308d
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发表时间：
2014-11
期刊：
影响因子：
--
通讯作者：
Laura Kersten;K. Harms;G. Hilt
中科院分区：
文献类型：
--
作者：
Laura Kersten;K. Harms;G. Hilt
本工作的目的是通过β-多羰基化合物的环化反应合成多环芳烃体系。用于β-聚羰基衍生物的有用的二烯烃是通过钴催化的末端烯烃和2，3-二甲基-1，3-丁二烯的加氢乙烯化产生的支链1，4-二烯。因此，成功地合成了一系列三羰基、四羰基和五羰基双酮。随后，在臭氧分解/环化反应序列中检查这些二价体。以较高的收率得到了多芳族衍生物，并将该方法应用于天然产物Kwanzoquinone A的合成。
The aim of this work was the synthesis of polyaromatic systems by cyclization of β-polycarbonyls. Useful synthons for β-polycarbonyl derivatives are branched 1,4-dienes generated by cobalt-catalyzed hydrovinylation of terminal alkenes and 2,3-dimethyl-1,3-butadiene. Thus, a series of tri-, tetra-, and pentacarbonyl synthons was successfully synthesized. Subsequently, these synthons were examined in an ozonolysis/cyclization reaction sequence. Polyaromatic derivatives were obtained in good yields and the method was applied in the synthesis of the natural product Kwanzoquinone A.