First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol.
We report the first synthesis of the unnatural enantiomer of desmosterol (ent-desmosterol). The sterol nucleus was constructed enantiospecifically, followed by stepwise addition of the side chain. Beginning with ent-androst-4-ene-3,17-dione, ent-desmosterol was synthesized in 13 steps and 20% yield. Protected ent-desmosterol was subjected to catalytic deuteration to afford ent-deuterocholesterol. Ent-desmosterol and ent-deuterocholesterol will be used to study the importance of sterol absolute configuration for sterol-lipid interactions in biophysical studies and in biological systems.
Westover
Emily J
EJ
Department of Molecular Biology and Pharmacology, Washington University School of Medicine, 660 S. Euclid Ave., St. Louis, MO 63110, USA.
Covey
Douglas F
DF
D002784:Cholesterol / Q000138:chemical synthesis* / Q000737:chemistry*; D003897:Desmosterol / Q000138:chemical synthesis* / Q000737:chemistry*; D003903:Deuterium; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D003897:Desmosterol; D002784:Cholesterol; D003903:Deuterium