Expedient and Practical Synthesis of CERT-Dependent Ceramide Trafficking Inhibitor HPA-12 and Its Analogues
Organic Letters2011Vol. 13(7), pp. 1642–1645
Citations Over TimeTop 14% of 2011 papers
Andrej Ďuriš, Tomáš Wiesenganger, Daniela Moravčíková, P. Baran, Jozef Kožíšek, Adam Daı̈ch, Dušan Berkeš
Abstract
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.
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