CHEMISTRY OF 10ALPHA-ESTR-4-EN-17BETA-OL-3-ONE AND SELECTED TRANSFORMATION PRODUCTS

Hydrogenation of estra-4,9(ll)-dien-17β-ol-3-one (1) gave 10α-estr-4-en-17β-ol-3-one (2), the parent member of a new series of steroids. Spectral studies indicate that ring B in this series has a boat conformation. This strained system is readily isomerized to 19-nortestosterone in acids and in base. Reduction with lithium aluminum tri-2-butoxyhydride gave the corresponding equatorial 3α-alcohol 7, which was converted into the 3-deoxy-Δ4 and -Δ5(6) olefinic analogs by hydrogenolysis with lithium in ethylamine. The C-4 double bond appears to shift to the corresponding C-5(6) olefin in the presence of strong base. Reduction of 2 with lithium-ammonia solutions gave 10α,5β-estra-17β-ol-3-one (10). © 1969, American Chemical Society. All rights reserved.