Novel synthesis of phytosphingosine from levoglucosenone

Phytosphingosine, (2S,3S,4R)-2-amino-1,3,4-octadecanetriol was prepared in 8.6% overall yield in 17 steps from levoglucosenone (1,6-anhydro-3,4-dideoxy-β-d-glycero-hex-3-enopyranos-2-ulose) by reduction of the carbonyl group, selective cis-oxyamination of the carbon-carbon double bond, oxidation of the 2-hydroxyl group to the carbonyl group, regioselective Baeyer-Villiger oxidation, reduction of the afforded lactone to the linear amino alcohol, oxidation of the primary hydroxyl group to the aldehyde, introduction of the hydrocarbon chain using a Wittig reaction, hydrogenation of the resulting carbon-carbon double bond, and deprotection.