The function of the carbonyl moiety at C-3 of steroid hormones in eliciting biological responses has been the subject of some study in this1 and other lab~ ratories.~~~ In the course of our search for claudogenic steroids, we needed to prepare estr-4-ene-3a, l7/3-diol by reduction of 19-nortestosterone with LiAlH4. Purification of the crude product gave estr-4- ene-3/3, 17P-diol and estra-3, 5-dien-