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学科主题: 天然产物有机化学
题名: General route to 2,4,5-trisubstituted piperidines from enantiopure b-amino esters. Total synthesis of pseudodistomin B triacetate and pseudodistomin F
其他题名: 通过光学纯β-氨基酯合成2,4,5-三取代哌啶烷的路线。 Pesudodistomin B triacetate and pseudodistomin F的全合成
作者: Ma DW(马大为) ; Sun HY(孙海鹰)
通讯作者: 马大为
刊名: J. Org. Chem.
发表日期: 2000-01-01
卷: 65, 期:19, 页:6009-6016
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所生命有机化学实验室
英文摘要: The michael addition reaction of enantiopure β-amino esters with methyl acrylate followed by dieckmann condensation and enol silyation affords the enol ethers 6, which are hydrogenated with catalysis by raney-Ni at 80 atm and 80℃ to provide 2,4,5-trisubstituted piperidines with high diastereoselectivity. In this case Ni-H attacks the C-C double bond from the direction of the 2-alkyl group to provide the products in which 2,4,5-trisubstrited groups are all cis to each other. While hydrogenation of enol ether 13 without a N-boc protecting group gives the product 15 in which the 4-hydroxy group and 5-ester moiety are trans to the 2-allkyl group. By using the diastereoselective hydrogenation products 9d and 9e as key intermediats, pseudodistomin B triacetate and pseudodistomin F are synthesized. The key steps for these transformations include curtius rearrangement and Julia olefination.
语种: 英语
相关网址: 查看原文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/15379
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
Ma DW,Sun HY. General route to 2,4,5-trisubstituted piperidines from enantiopure b-amino esters. Total synthesis of pseudodistomin B triacetate and pseudodistomin F[J]. J. Org. Chem.,2000,65(19):6009-6016.
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