Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
J Org Chem. 2010 Dec 17;75(24):8728-31. doi: 10.1021/jo102038q. Epub 2010 Nov 23.
An efficient stereoselective synthesis of fully protected (2S,4R)-4-methylpipecolic acid has been developed. The synthesis was achieved by initial asymmetric α-alkylation of glycine with a chiral iodide, affording the linear precursor as a single stereoisomer. Subsequent aldehyde formation using OsO(4)/NaIO(4) followed by immediate intramolecular cyclization afforded an enamine that was then subjected to hydrogenation to give the final compound in 23% yield over 10 steps.
已开发出一种高效的全保护（2S,4R）-4-甲基哌啶酸的立体选择性合成方法。该合成方法通过甘氨酸与手性碘化物的初始不对称α-烷基化反应实现，得到了单一立体异构体的线性前体。随后使用 OsO(4)/NaIO(4)进行醛形成，然后立即进行分子内环化，得到烯胺，然后将其氢化得到最终化合物，总收率为 10 步中的 23%。
