Total Synthesis of (+)-Korupensamine B via an Atropselective Intermolecular Biaryl Coupling

Total Synthesis of (+)-Korupensamine B via an Atropselective Intermolecular Biaryl Coupling
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DOI:
10.1021/ja1065202
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发表时间:
2010-10-13
影响因子:
15
通讯作者:
Lipshutz, Bruce H.
Lipshutz, Bruce H.
中科院分区:
化学1区
文献类型:
--
作者:
Huang, Shenlin;Petersen, Tue B.;Lipshutz, Bruce H.

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报道了非外消旋Korupensamine B的不对称全合成。它包括一个新设计的和高度反式非对映选择性(>20:1 dr)的路线,以四氢异喹啉环和一个前所未有的atropnonaqueoselective铃木-宫浦耦合建设的完全成型的萘异喹啉框架,调用π堆叠作为一个可能的来源的立体控制。
The asymmetric total synthesis of nonracemic korupensamine B is reported. It includes a newly designed and highly trans-diastereoselective (>20:1 dr) route to the tetrahydroisoquinoline ring and an unprecedented atropdiastereoselective Suzuki-Miyaura coupling for construction of the fully fashioned naphthylisoquinoline framework that invokes pi stacking as a possible source of stereocontrol.