Asymmetric total syntheses of (-)-antofine and (-)-cryptopleurine using (R)-(E)-4-(tributylstannyl)but-3-en-2-ol
Asymmetric total syntheses of (-)-antofine and (-)-cryptopleurine using (R)-(E)-4-(tributylstannyl)but-3-en-2-ol
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DOI：
10.1021/jo049820a
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发表时间：
2004-04-30
影响因子：
3.6
通讯作者：
Kim, D
中科院分区：
文献类型：
--
作者：
Kim, S;Lee, T;Kim, D
本文报道了具有代表性的菲并吲哚里西啶和菲并喹里西啶生物碱（-）-antofine和（-）-cryptopleurine的不对称全合成。通过使用手性结构单元（R）-9和具有手性全转移的Overman重排，实现了对映体纯形式的关键中间体12的有效合成途径。成功地解决了构建吡咯烷和哌啶环的问题，主要是通过分别使用闭环复分解反应和交叉复分解反应。
The asymmetric total syntheses of the representative phenanthroindolizidine and phenanthro-quinolizidine alkaloids, (-)-antofine and (-)-cryptopleurine, are described. An efficient synthetic pathway to the key intermediate 12, in enantiomerically pure form, was achieved by using a chiral building block (R)-9 and the Overman rearrangement with a total transfer of chirality. The problem of constructing the pyrrolidine and piperidine rings was successfully addressed, primarily by using a ring-closing metathesis reaction and a cross-metathesis reaction, respectively.