On the synthesis of protopine alkaloids
On the synthesis of protopine alkaloids
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DOI：
10.1021/jo071038y
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发表时间：
2007-09-14
影响因子：
3.6
通讯作者：
Orito, Kazuhiko
中科院分区：
文献类型：
--
作者：
Wada, Yasuhiro;Kaga, Harumi;Orito, Kazuhiko
为了合成原阿片碱生物碱，我们研究了基于通过单线态氧氧化使茚并[2，1-a][3]苯并氮杂卓扩环，然后将所得10元酮-内酰胺的酰胺羰基转化为亚甲基的反应顺序，这是完成合成的最后一步。以烷氧基取代的1-（2-溴苄基）-3-苯并氮杂卓-2-酮为原料，经Bischler-Napieralski环合反应，合成了茚并[2，1-a][3]苯并氮杂卓类化合物。考察了取代基的空间效应。
[GRAPHICS]For the synthesis of protopine alkaloids, we studied a reaction sequence based on a ring enlargement of indeno[2,1-a][3]benzazepines by a singlet oxygen oxygenation, followed by conversion of an amide carbonyl group of the resultant 10-membered keto-lactam to a methylene group, which is the last step for completion of the synthesis. The key substances, indeno[2,1-a][3]benzazepines, were prepared by Bischler-Napieralski cyclization of alkoxy-substituted 1-(2-bromobenzyl)-3-benzazepin-2-ones. Steric effects of the substituents in this synthesis were examined.