Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237 Bratislava, Slovakia.
Org Lett. 2011 Apr 1;13(7):1642-5. doi: 10.1021/ol2001057. Epub 2011 Feb 25.
The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereochemistry of the first inhibitor of CERT-dependent ceramide trafficking HPA-12 from (R,R)-anti- to the (R,S)-syn-enantiomer. Due to the expeditiousness of production and inexpensive conditions developed, a series of alkyl- and aryl-substituted analogues of HPA-12 is also reported.
基于结晶诱导的不对称转变 (CIAT) 方法，完成了 1-取代的 3-氨基丁烷-1,4-二醇的顺式和反式非对映异构体的实用立体发散途径。这导致了对第一个 CERT 依赖性神经酰胺转运抑制剂 HPA-12 的报道立体化学的修订，从（R,R）-反式到（R,S）-顺式对映异构体。由于生产的迅速和开发的廉价条件，还报道了一系列 HPA-12 的烷基和芳基取代类似物。
