Efficient synthetic access to the hetisine C20-diterpenoid alkaloids.: A concise synthesis of nominine via oxidoisoquinolinium-1,3-dipolar and dienamine-Diels-Alder cycloadditions
Efficient synthetic access to the hetisine C20-diterpenoid alkaloids.: A concise synthesis of nominine via oxidoisoquinolinium-1,3-dipolar and dienamine-Diels-Alder cycloadditions
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DOI：
10.1021/ja0625430
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发表时间：
2006-07-12
影响因子：
15
通讯作者：
Gin, David Y.
中科院分区：
文献类型：
--
作者：
Peese, Kevin M.;Gin, David Y.
报道了一种合成Hetisine C20-二萜生物碱的简明方法。采用双环加成策略，以15步的顺序完成了(±)-诺明的全合成。该合成的主要特征包括可逆的分子内4-氧代异喹啉甜菜碱偶极环加成反应和吡咯烷诱导的二烯胺异构化/Diels−Alder级联反应。
A concise synthetic approach to the hetisine C20-diterpenoid alkaloids is reported. The total synthesis of (±)-nominine was accomplished in a 15-step sequence employing a dual cycloaddition strategy. Key features of the synthesis include a reversible intramolecular 4-oxidoisoquinolinium betaine dipolar cycloaddition in conjunction with a pyrrolidine-induced dienamine isomerization/Diels−Alder cascade.