SUBSTITUTION-REACTIONS OF 2-PHENYLSULFONYL-PIPERIDINES AND 2-PHENYLSULFONYL-PYRROLIDINES WITH CARBON NUCLEOPHILES - SYNTHESIS OF THE PYRROLIDINE ALKALOIDS NORRUSPOLINE AND RUSPOLINONE
SUBSTITUTION-REACTIONS OF 2-PHENYLSULFONYL-PIPERIDINES AND 2-PHENYLSULFONYL-PYRROLIDINES WITH CARBON NUCLEOPHILES - SYNTHESIS OF THE PYRROLIDINE ALKALOIDS NORRUSPOLINE AND RUSPOLINONE
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DOI：
10.1016/s0040-4020(01)86388-2
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发表时间：
1991-02-11
期刊：
影响因子：
2.1
通讯作者：
LEY, SV
中科院分区：
文献类型：
--
作者：
BROWN, DS;CHARREAU, P;LEY, SV
通过用苯亚磺酸处理相应的N-酰基动物，制备了几种2-苯基磺酰基-哌啶和2-苯基磺酰基-吡咯烷。在与各种碳亲核试剂反应时，这些砜产生了良好产率的取代产物。这些研究中使用的典型亲核试剂是在路易斯酸存在下衍生自格氏试剂和卤化锌以及甲硅烷基烯醇醚、甲硅烷基乙烯酮缩醛、烯丙基硅烷和三甲基甲硅烷基氰化物的有机金属试剂。这些方法用于合成两种天然产物生物碱； Norruspoline (38) 和 Ruspolinone (40)。
Several 2-phenylsuphonyl-piperidines and -pyrrolidines were prepared from the corresponding N-acyl animals by treatment with benzenesulphinic acid. On reaction with various carbon nucleophiles these sulphones gave good yields of substitution products. Typical nucleophiles used in these studies were organometallic reagents derived from Grignard reagents and zinc halide together with silyl enol ethers, silyl ketene acetals, allylsilanes and trimethylsilyl cyanide in the presence of a Lewis acid. These methods were employed in the synthesis of two natural product alkaloids; Norruspoline (38) and Ruspolinone (40).