REGIO- AND STEREOSELECTIVE 1,4-REDUCTIONS OF METHYLATED, CROSS-CONJUGATED STEROIDAL CYCLOHEXADIENONES

Article abstract of DOI:10.1016/S0040-4039(00)97488-4

Regio- and stereoselectivities in conjugate reductions of steroidal 3-oxo-1,4-diene substrates, effected either directly by Fe(CO)5-NaOH-H2O in methanol solution or in two steps by NaBH4 reduction/Jones oxidation, depend on the substitution pattern of ring A.C(1) and C(2) methylated derivatives furnish Δ¹-products with 5β-stereochemistry, whereas C(4) methylated and unsubstituted steroids both afford Δ⁴-derivatives.