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Synfacts 2011(7): 0698-0698  
DOI: 10.1055/s-0030-1260480
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of HPA-12

Contributor(s): Philip Kocienski
A. Ďuriš, T. Wiesenganger, D. Moravčíková, P. Baran, J. Kožíšek, A. Daïch, D. Berkeš*
Slovak University of Technology, Bratislava, Slovakia; Juniata College, Huntingdon, USA; University of Le Havre, France
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Publikationsdatum:
17. Juni 2011 (online)

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Significance

HPA-12 is the first specific inhibitor of sphingomyelin biosynthesis in mammalian cells and an important lead for the treatment of dis­eases dependent on ceramide trafficking. The key step in the synthesis of HPA-12 is the 3-component asymmetric Mannich reaction leading to the γ-oxo-α-amino acid D. The high dr of this ­reaction is a consequence of crystallization-­induced diastereoselection.