Journal
ORGANIC LETTERS
Volume 15, Issue 11, Pages 2869-2871Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol401101u
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- Japan Society for the Promotion of Science (JSPS), Global COE Program
- University of Tokyo, MEXT, Japan
- Japan Science Technology Agency (JST)
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In response to Berkes's report revising the stereochemistry of HPA-12, an important ceramide-trafficking inhibitor that was discovered and synthesized and its stereochemistry determined in 2001, the synthesis and the stereochemistry were reinvestigated. A large-scale synthetic method for HPA-12 based on a Zn-catalyzed asymmetric Mannich-type reaction in water was developed. Single crystals of HPA-12 for X-ray crystallographic analysis were obtained from ethyl propionate/n-hexane, and the stereochemistry was definitely determined to be 1R,3S, consistent with Berkes's revised structure.
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