一种合成尼古丁和新烟草碱类似物的新型高效方法。
A New and Efficient Approach to the Synthesis of Nicotine and Anabasine Analogues.
作者信息
Huang Kun, Ortiz-Marciales Margarita, De Jesús Melvin, Stepanenko Viatcheslav
机构信息
Department of Chemistry, University of Puerto Rico-Humacao, CUH Station, Humacao, Puerto Rico 00791-4300, USA.
出版信息
J Heterocycl Chem. 2009 Nov 6;46(6):1252-1258. doi: 10.1002/jhet.233.
Abstract
A straightforward and practical approach was established for the synthesis of nicotine and anabasine analogues by the cyclization of mesylated 1-(3-pyridinyl)-1,4, and 1,5-diol derivatives to form the pyrrolidino or piperidino fragments. Nicotine analogue (S)-15 was prepared with good enantioselectivity using the developed azacyclization procedure of nonracemic (R)-1-pyridin-3-yl-butane-1,4-diol, which was obtained by the borane-mediated reduction of ketone 12 in the presence of the spiroborate ester derived from diphenyl prolinol and ethylene glycol.
摘要
通过甲磺酰化的1-(3-吡啶基)-1,4-二醇和1,5-二醇衍生物环化以形成吡咯烷基或哌啶基片段，建立了一种合成尼古丁和新烟草碱类似物的直接且实用的方法。使用所开发的非外消旋(R)-1-吡啶-3-基-丁烷-1,4-二醇的氮杂环化程序，以良好的对映选择性制备了尼古丁类似物(S)-15，该非外消旋(R)-1-吡啶-3-基-丁烷-1,4-二醇是通过在由二苯基脯氨醇和乙二醇衍生的硼酸酯存在下硼烷介导的酮12的还原反应获得的。
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