Chemistry of Lactam-Derived Vinyl Phosphates: Stereoselective Synthesis of (+)-Fagomine

Chemistry of Lactam-Derived Vinyl Phosphates: Stereoselective Synthesis of (+)-Fagomine
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DOI:
10.1055/s-0028-1088202
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发表时间:
2009-04-01
期刊:
影响因子:
2
通讯作者:
Occhiato, Ernesto G.
Occhiato, Ernesto G.
中科院分区:
化学4区
文献类型:
--
作者:
Bartali, Laura;Scarpi, Dina;Occhiato, Ernesto G.

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提出了基于内酰胺衍生的乙烯基磷酸酯的 Pd 催化甲氧基羰基化反应和烯胺双键的立体选择性硼氢化-氧化反应的 (+)-fagomine 的合成。通过八步从已知内酰胺中获得目标产物,总产率为 23%。
The synthesis of (+)-fagomine, based on the Pd-catalyzed methoxycarbonylation reaction of a lactam-derived vinyl phosphate and the stereoselective hydroboration-oxidation of the enamine double bond, is presented. The target product is obtained in 23% overall yield in eight steps from a known lactam.