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不对称全合成与弓蕊藤碱相关的吲哚生物碱羟基阿朴啡,羟基阿朴啡碱,弓蕊罂粟碱,(E)-16-表-Nor 鸦片碱 B 和扣米定。

Asymmetric Total Synthesis of Sarpagine-Related Indole Alkaloids Hydroxygardnerine, Hydroxygardnutine, Gardnerine, (E)-16-epi-Normacusine B, and Koumine.

机构信息

Graduate School of Pharmaceutical Sciences, Chiba University , 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan.

出版信息

Org Lett. 2016 Apr 15;18(8):1912-5. doi: 10.1021/acs.orglett.6b00661. Epub 2016 Apr 1.

Abstract

Sarpagine-related indole alkaloids (-)-hydroxygardnerine, (+)-hydroxygardnutine, (-)-gardnerine, (+)-(E)-16-epi-normacusine B, and (-)-koumine were divergently synthesized via a common intermediate possessing a piperidine ring with an exocyclic (E)-ethylidene side chain, which was constructed by a gold(I)-catalyzed 6-exo-dig cyclization strategy.

摘要

薤白相关吲哚生物碱 (-)-羟基缬草碱、(+)-羟基缬草宁、(-)-缬草碱、(+)-(E)-16-表-诺卡枯林 B 和 (-)-扣米因通过具有哌啶环和外消旋 (E)-亚乙基侧链的共同中间体进行了发散合成,该中间体通过金 (I)-催化的 6-endo-dig 环化策略构建。

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