Studies on Steroid Conjugates. III. New Syntheses of 2-Methoxyestrogens

The new synthetic routes leading to the 2-methoxyestrogens from the readily available compounds have been investigated. Utilization of both Friedel-Crafts and Baeyer-Villiger reactions with estrone and estradiol 3-methyl ethers gave the desired 2-methoxyestrogens in overall yield of ca. 50%. Fries rearrangement with estrone acetate and Friedel-Crafts reaction with 2-methoxy-3-deoxyestrogens were also undertaken. The chemical shifts of the aromatic protons of the 2, 3-substituted estratrienes are collected in Table I and II.