Aza-steroids. Part VI. Approaches based on furfuraldehyde

Abstract

An approach to aza-steroids, starting from furfuraldehyde and based on Robinson's work in the equilenin series, has not been successful. Although furfuraldehyde condensed with the appropriate methyl ketones, acid hydrolysis of the adducts led to γ-(arylfuryl)propionic acids (VIII) rather than the desired 7-aryl-4,7-dioxoheptanoic acids. Reactions of these acids (VIII) and the compound 1,2-dihydro-5-hydroxybenz[e]inden-3-one (IX) are discussed.