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Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators
Synthesis ( IF 2.6 ) Pub Date : 2020-08-10 , DOI: 10.1055/s-0040-1707222 Kamal Kumar 1 , Mohammad Rehan 1 , Jana Flegel 1, 2 , Franziska Heitkamp 1, 2 , Jorgelina L. Pergomet 1 , Felix Otte 2 , Carsten Strohmann 2
中文翻译:
3,3'-哌啶基螺氧杂吲哚的不对称合成和作为新的Hedgehog通路调节剂的立体特异性Cycloadducts的发现
更新日期:2020-08-11
Synthesis ( IF 2.6 ) Pub Date : 2020-08-10 , DOI: 10.1055/s-0040-1707222 Kamal Kumar 1 , Mohammad Rehan 1 , Jana Flegel 1, 2 , Franziska Heitkamp 1, 2 , Jorgelina L. Pergomet 1 , Felix Otte 2 , Carsten Strohmann 2
Affiliation
In memory of Prof. Dr. Rolf Huisgen
Abstract
An enantioselective hetero-Diels–Alder reaction of alkylidene oxindoles and 2-aza-3-silyloxy-1,3-butadienes, catalyzed by divalent transition metal complexes with N,N′-dioxide ligands offered an efficient access to natural-product-based 3,3′-piperidinoyl spirooxindole class of small molecules. exo-Cycloadducts formed via stereospecific cycloaddition with Z-olefin displayed potent activity in modulation of hedgehog pathway.
中文翻译:
3,3'-哌啶基螺氧杂吲哚的不对称合成和作为新的Hedgehog通路调节剂的立体特异性Cycloadducts的发现
纪念Rolf Huisgen教授
抽象
亚烷基吲哚和2-氮杂-3-甲硅烷氧基-1,3-丁二烯的对映选择性杂Diels-Alder反应,由具有N,N'-二氧化物配体的二价过渡金属配合物催化,可有效地获得基于天然产物的3,3'-哌啶子基螺氧基吲哚类小分子。通过立体特异性环加成反应与Z-烯烃形成的exo-环加合物在刺猬信号通路的调节中显示出强大的活性。