Crystal Structure and Synthesis of 17α-Acetoxy-6,7-Epoxypregn-4-ene-3,20-dione

The document describes the synthesis and X-ray structure determination of a new antiandrogen compound, 17α-acetoxy-6,7-epoxypregn-4-ene-3,20-dione, which could potentially be used in the treatment of androgen-mediated diseases such as prostate cancer, hirsutism, acne, seborrhea, androgenic alopecia, and benign prostatic hyperplasia. The compound was synthesized from commercially available 17α-acetoxyprogesterone, with a 60% yield after treatment with chloranil and a 70% yield following epoxidation with m-chloroperbenzoic acid. The crystal structure was determined using X-ray data collected at 298(2)K without absorption correction, solved by direct methods, and refined by full-matrix least-squares. The molecule consists of three six-membered rings and one five-membered ring, with bond lengths and angles that are mostly normal. The molecules in the crystal are packed at normal van der Waals distances, and there are two intermolecular C-H...O interactions. The study provides detailed information on the synthesis and structure of the compound, which could be important for the development of treatments for androgen-dependent conditions.