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Org Lett. 2011 Apr 1;13(7):1642-5. doi: 10.1021/ol2001057. Epub 2011 Feb 25.

Expedient and practical synthesis of CERT-dependent ceramide trafficking inhibitor HPA-12 and its analogues.

Author information

1
Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237 Bratislava, Slovakia.

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.

PMID:
21351771
DOI:
10.1021/ol2001057
[Indexed for MEDLINE]

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