Tetrahedron Letters p. 6081 - 6084 (1991)
Update date:2022-07-30
Topics: Regioselectivity Yield NMR spectroscopy Stereochemistry Stereoselective synthesis Purification Catalysis Steroids Isotopic Labeling Pd-Catalyzed Synthetic Methodology Deuterium (D)
Rabinowitz
A simple and highly stereoselective synthesis of [4α-2H]- and [4α-3H]-Δ5-3β-hydroxysteroids is presented. Palladium(O)-mediated borodeuteride reduction of readily-available cholest-5-en-3β,4β-diol cyclic carbonate provides [4α-2H]-Δ5-and Δ4-cholesterol in a 12:1 ratio. Reduction of [4α-3H]-cholest-5-ene-3β,4β-diol cyclic carbonate with NaB1H4 and Pd(O) resulted in [4β-3H]-cholesterol.
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