Consecutive 6-endo trigonal cyclisations from polyene acyl radical intermediates leading to decalone and perhydrophenanthrone ring constructions
Consecutive 6-endo trigonal cyclisations from polyene acyl radical intermediates leading to decalone and perhydrophenanthrone ring constructions
复制标题
多烯酰基自由基中间体的连续 6-内三角环化导致十酮和全氢菲酮环结构
DOI：
10.1039/p19960000031
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发表时间：
1996
期刊：
影响因子：
--
通讯作者：
H. Simonian
中科院分区：
文献类型：
--
作者：
Ligong Chen;G. Gill;G. Pattenden;H. Simonian
合成了一系列取代的5，9-二烯硒酸硒苯酯，即15 a，25，26，27，42和52，并研究了它们与Bu_3SnH-AIBN的反应。二烯酯15 a、42和52显示出通过从相应的5，9-二烯酰基中间体开始的连续的6-内消旋环化模式分别产生十氢萘酮和全氢菲蒽酮衍生物，即19、43和53。相比之下，在C-9处缺乏烷基取代的5，9-二烯酸酯25和27反而分别环化成茚满酮36和37，并且6-甲基取代的类似物26在用Bu 3SnH-AIBN处理时仅产生环戊酮38。
A range of substituted Se-phenyl 5,9-dieneselenoates, viz. 15a, 25, 26, 27, 42 and 52, have been synthesised and their reactions with Bu3SnH–AIBN investigated. The diene esters 15a, 42 and 52 are shown to lead to decalone and to perhydrophenanthrone derivatives, viz. 19, 43 and 53, respectively, via consecutive 6-endo trig modes of cyclisations starting from the corresponding 5,9-diene acyl radical intermediates. By contrast, the 5,9-dienoates 25 and 27 lacking alkyl substitution at C-9 instead underwent cyclisation to the indanones 36 and 37, respectively, and the 6-methyl substituted analogue 26 produced only the cyclopentanone 38 on treatment with Bu3SnH–AIBN.