百部定碱假定结构的全合成：错误归属的最终证明。
Total synthesis of the putative structure of stemonidine: the definitive proof of misassignment.
作者信息
Sánchez-Izquierdo Francisco, Blanco Pilar, Busqué Félix, Alibés Ramón, de March Pedro, Figueredo Marta, Font Josep, Parella Teodor
机构信息
Universitat Autonoma de Barcelona, Departament de Química, 08193 Bellaterra, Spain.
出版信息
Org Lett. 2007 Apr 26;9(9):1769-72. doi: 10.1021/ol070486p. Epub 2007 Mar 31.
[structure: see text] The total synthesis of the putative structure of the Stemona alkaloid stemonidine has been completed. The key transformations include a 1,3-dipolar cycloaddition of a chiral nitrone derived from (S)-prolinol and a spirolactonization process involving the generation of the critical stereocenter. The NMR data of the synthetic material do not match those reported for the natural product. It is concluded that the structure assigned to stemonidine is incorrect, and it must be reassigned as stemospironine.
[结构：见正文]百部生物碱百部定碱推定结构的全合成已完成。关键转化包括由(S)-脯氨醇衍生的手性硝酮的1,3-偶极环加成反应以及涉及关键立体中心生成的螺内酯化过程。合成材料的核磁共振数据与天然产物报道的数据不匹配。得出的结论是， assigned to stemonidine的结构是不正确的，它必须重新指定为百部螺碱。 （注：原文中“assigned to stemonidine”表述有误，推测正确表述可能是“assigned to stemonidine”，翻译时保留了原文错误表述）
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