Syntheses of cis- and trans-Jamtine and Their N-Oxides via a Benzyl Configuration-Inversion Approach
Syntheses of cis- and trans-Jamtine and Their N-Oxides via a Benzyl Configuration-Inversion Approach
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通过苄基构型反转方法合成顺式和反式 Jamtine 及其氮氧化物
DOI：
10.1055/s-0037-1610745
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发表时间：
2020
期刊：
影响因子：
2
通讯作者：
Zheng Huaiji
中科院分区：
文献类型：
--
作者：
Liu Zhigang;Wang Zhengshen;Li Yujie;Zhang Qiang;Gao Jin-Ming;Zheng Huaiji
摘要报道了四氢异喹啉生物碱Jamtin及其同分异构体的新合成方法。合成策略依赖于一锅共轭还原/Robinson环化序列和有效的氧化/还原方法的苄基构型反转。合成了茉莉酸异构体的N-氧化物衍生物，并用X-射线单晶分析进行了确证。此外，对四种可能的氮氧化物结构进行了密度泛函理论计算，以进一步了解天然产物的结构，并与合成氮氧化物的结构进行了比较，因为合成衍生物的核磁共振数据与天然氮氧化物的核磁共振数据不匹配。
Abstract A novel synthesis of the tetrahydroisoquinoline alkaloid jamtine and its epimer is reported. The synthetic strategy hinges on a one-pot conjugate reduction/Robinson cyclization sequence and an efficient benzyl configuration inversion by an oxidation/reduction approach. The N-oxide derivatives of the jamtine isomers were also synthesized and identified by X-ray crystallographic analysis. Additionally, a density functional theory calculation for the four possible N-oxide structures was exploited to gain further insight into the structure of the natural product in comparison to those of the synthetic N-oxides, because the NMR data of the synthetic derivatives did not match those reported for natural jamtine N-oxide.