Total Syntheses of Naucleamides A-C and E, Geissoschizine, Geissoschizol, (E)-Isositsirikine, and 16-epi-(E)-Isositsirikine
Total Syntheses of Naucleamides A-C and E, Geissoschizine, Geissoschizol, (E)-Isositsirikine, and 16-epi-(E)-Isositsirikine
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核酸酰胺 A-C 和 E、Geissoschizine、Geissoschizol、(E)-Isositsirikine 和 16-epi-(E)-Isositsirikine 的全合成
DOI：
10.1021/acs.orglett.7b00983
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发表时间：
2017
期刊：
影响因子：
5.2
通讯作者：
Jia Yanxing
中科院分区：
文献类型：
--
作者：
Li Lei;Aibibula Paruke;Jia Qianlan;Jia Yanxing
提出了一种对映选择性全合成八种单萜类吲哚生物碱的发散方法。该方法只需要6-8个步骤就可以首次合成核酰胺A-C和E，并且可以在10-11个步骤中从市售的巴豆醛中有效地合成geissoschizine， geissoschizol, (E)-异西sirikine和16-epi-(E)-异西sirikine。该合成以一锅有机催化的不对称Michael加成/ Pictet-Spengler反应为特征。值得注意的是，通过对核酰胺A的氧化环化，实现了核酰胺E的仿生合成。
A divergent approach for the enantioselective total synthesis of eight monoterpenoid indole alkaloids was developed. The approach allows the first total syntheses of naucleamides A–C and E in only 6–8 steps and also enables the efficient synthesis of geissoschizine, geissoschizol, (E)-isositsirikine, and 16-epi-(E)-isositsirikine in 10–11 steps from commercially available crotonic aldehyde. The synthesis features a one-pot organocatalyzed asymmetric Michael addition/Pictet–Spengler reaction. Notably, biomimetic synthesis of naucleamide E was achieved by oxidative cyclization of naucleamide A.