A novel inhibitor of ceramide trafficking from endoplasmic reticulum to the site of sphingomyelin synthesis.

VOLUME 276 (2001) PAGES 43994–44002 In the work indicated above, we depicted the stereochemistry of active HPA-12 to be 1R,3R. However, Ďuriš et al. (Ďuriš, A., Wiesenganger, T., Moravčíková, D., Baran, P., Kožíšek, J., Daïch, A., and Berkeš, D. (2011) Expedient and practical synthesis of CERT-dependent ceramide trafficking inhibitor HPA-12 and its analogues. Org Lett. 13, 1642–1645) recently proposed the stereochemistry of active HPA-12 to be 1R,3S. In response to this proposal, we have developed a gram-scale preparation method of HPA-12 and confirmed the (1R,3S) stereochemistry of active HPA-12 by x-ray crystallographic analysis (Ueno, M., Huang, Y. Y., Yamano, A., and Kobayashi, S. (2013) Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by x-ray crystallography analysis. Org. Lett. 15, 2869–2871). The initial incorrect stereochemical assignment is probably because of an unexpected epimerization at the benzylic position occurred in an intermediate under harsh conditions in the synthetic route that we used previously (Ueno et al.). Accordingly, the stereochemistry of HPA-12 in this work should be corrected: (1R,3R), (1S,3S), (1R,3S), and (1S,3R) should be read as (1R,3S), (1S,3R), (1R,3R), and (1S,3S), respectively.