Tetrahedron p. 1229 - 1239 (2018)
Update date:2022-08-04
Topics:
Legendre, Sarah V.A.-M.
Jevric, Martyn
Klepp, Julian
Sumby, Christopher J.
Greatrex, Ben W.
A Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines with primary and secondary amines has been developed which affords 4-hydroxy-3-aminoketones. The aza-Michael products were reduced using non-selective NaBH4/MeOH or diastereoselective (up to 92:8) SnCl4/NaBH4 conditions yielding (1R?,3S?)-3-amino-1,4-diols in up to 97% and 70% yield respectively. The major reduction product was converted in two steps to (±)-HPA-12, which is an inhibitor of the cytosolic ceramide transporting protein.
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