D-ring allyl derivatives of 17β- and 17α-estradiols: Chemical synthesis and 13C NMR data

Article abstract of DOI:10.1016/S0039-128X(97)00067-6

We report the ¹³ C NMR data for 17β-estradiol, 17α-estradiol, and a series of ten 17β- or 17α-estradiol derivatives bearing an allyl group on the D-ring (at C-17, C-16, and C-15 positions). The target 17β-OH estradiol derivatives were synthesized from estrone by well known obtained by a modified Mitsunoba alcohol inversion of the allyl group (17α, 17β, 16α, 16β, and 15β) and two alcohol stereochemistries (17β and 17α) of the D- ring were studied, resulting in an important source of data. The effect of allyl-positioning and alcohol stereochemistry on ¹³C NMR chemical shifts was also identified, producing important points of comparison for other steriod analogs.