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First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol
Emily J Westover1, Douglas F Covey
1Department of Molecular Biology and Pharmacology, Washington University School of Medicine, 660 S. Euclid Ave., St. Louis, MO 63110, USA.
Abstract:
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.