Concise, stereoselective route to the four diastereoisomers of 4-methylproline
Concise, stereoselective route to the four diastereoisomers of 4-methylproline
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DOI：
10.1021/np070673w
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发表时间：
2008-05-01
影响因子：
5.1
通讯作者：
Munro, Murray H. G.
中科院分区：
文献类型：
--
作者：
Murphy, Annabel C.;Mitova, Maya I.;Munro, Murray H. G.
4-甲基脯氨酸是在许多肽次级代谢物中发现的一种稀有氨基酸，其完整的立体化学表征常常受到长反应序列或参考样品合成中低立体选择性的阻碍。提出了通过简洁的立体选择性路线制备4-甲基脯氨酸的四种非对映异构体的方法，该路线具有后期立体发散的六步路线，顺式和反式的立体选择性良好（分别为75％和88％de），并且总收率良好（累积收率30-40％）。还提供了有关立体异构体马菲衍生物的附加数据。
The full stereochemical characterization of 4-methylproline, a rare amino acid found in a number of peptidic secondary metabolites, has often been hindered by long reaction sequences or low stereoselectivity in the synthesis leading to reference samples. The preparation of the four diastereoisomers of 4-methylproline by a concise and stereoselective route is presented and features a six-step route with late-stage stereodivergence, good stereoselectivity for both cis- and trans-series (75% and 88% de, respectively), and good overall yields (cumulative yields of 30-40%). Additional data on the Marfey's derivatives of the stereoisomers are also presented.