STUDIES DIRECTED TOWARD SYNTHESIS OF QUASSINOIDS VII .- CONVERSION OF CHENODEOXYCHOLIC ACID TO A δ-LACTONE QUASSINOID ANALOG AND GENERATION OF A-RING DIOSPHENOL ACETATE DERIVATIVES OF DEOXYCHOLIC ACID

Article abstract of DOI:10.1016/0039-128X(80)90141-5

Chenodeoxycholic acid was converted to a new 5,14-epi-28,30-dinorquassinoid analog.Two isomeric A-ring diosphenol acetate derivatives of deoxycholic acid were synthesized.A 3-oxo-5β-steroid was transformed to a 4-acetoxy-3-oxo-Δ⁴-steroid by treatment with base and oxygen or to a 2-acetoxy-3-oxo-Δ²-steroid by reaction with cupric chloride in refluxing acetic acid followed by acetylation.Ketene extrusion is a characteristic mass spectral fragmentation of these diosphenol acetates.