Stereoselective Sequence toward Biologically Active Fused Alkylidenecyclobutanes

Stereoselective Sequence toward Biologically Active Fused Alkylidenecyclobutanes
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DOI:
10.1021/acs.orglett.7b00724
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发表时间:
2017-04-21
期刊:
影响因子:
5.2
通讯作者:
Didier, Dorian
Didier, Dorian
中科院分区:
化学1区
文献类型:
--
作者:
Baumann, Andreas N.;Eisold, Michael;Didier, Dorian

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结合环丁烯基金属物种的有效制备,高产率的交叉偶联反应,和高度非对映选择性的[4 + 2]-环加成,导致打开一个新的路线走向稠合的亚烷基环丁烷的合成含有多达五个连续的立体中心。新的复杂的架构,类似物的protoilluminescent骨架,获得了一个非常有效的方式,并与最少的步骤从商业来源,并测试其对白血病细胞系HL 60的细胞毒性。
Combining an efficient preparation of cyclobutenylmetal species, high-yielding cross-coupling reactions, and highly diastereoselective [4 + 2]-cycloaddition led to opening a new route toward the synthesis of fused alkylidenecyclobutanes containing up to five consecutive stereocenters. New complex architectures, analogues to protoilludane skeletons, were obtained in a very efficient manner and with a minimum number of steps starting from commercial sources and were tested for their cytotoxicity against leukemia cell lines HL60.