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Formal amide insertion strategy for the synthesis of anatoxin-a using rhodium catalysis
Tetrahedron ( IF 2.1 ) Pub Date : 2016-02-10 10:27:30
Masato Kono, Shingo Harada, Yasumasa Hamada, Tetsuhiro Nemoto

A formal synthesis of anatoxin-a was accomplished by using rhodium-catalyzed formal amide insertion reaction. The key reaction was performed on a gram scale using 0.4 mol % of Rh2(NHCOtBu)4 catalyst, affording a 9-azabicyclo[4.2.1]nonane derivative in good yield. The nitrogen-bridged molecule was converted to Wiseman's intermediate through diastereoselective reduction, site-selective deoxygenation and functional group interconversions.

中文翻译:

铑催化合成酰胺酶-a的形式酰胺插入策略

通过使用铑催化的正式酰胺插入反应,可以完成anatoxin-a的正式合成。使用0.4mol%的Rh 2(NHCO t Bu)4催化剂以克为单位进行关键反应,以良好的收率得到9-氮杂双环[4.2.1]壬烷衍生物。氮桥联分子通过非对映选择性还原,位点选择性脱氧和官能团互变而转化为Wiseman中间体。
更新日期:2016-02-11
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