CONDENSATION OF GLYOXYLIC ACID WITH 5ALPHA-ANDROSTANOLONE

The condensation of 5α-androstanolone with glyoxylic acid gave steroids with an α-hydroxyacetic acid side chain at C-2. This side chain then reacts further with the C-3 carbonyl group to give ring-A-fused lactols. The chemistry of these lactols was studied, and the lactols were used to synthesize the novel ring-A-fused pyridazone 6. When the condensation reaction was carried out in refluxing methanol, the C-2 trans-ylidene acetic acid derivative was isolated. The chemistry of these acids was studied, and their derivatives were used for synthesis of ring-A-fusedγ-lactones. © 1969, American Chemical Society. All rights reserved.