63608-63-9Relevant academic research and scientific papers
Steroids, L. Ring D Cleavage of D-Trisubstituted Steroids
Vincze, Iren,Somlai, Csaba,Schneider, Gyula
, p. 1103 - 1108 (2007/10/02)
In alkaline medium, 3β,17β-dihydroxy-15-(hydroxymethylene)androst-5-en-16-one (2a) is cleaved in two ways to give D-seco compounds.Dilute bases in protic solvents cause 1,3-dicarbonyl splitting to the 15-formyl-15,16-seco-16-oic acid 3, while the use of sodium methanolate in benzene solution gives rise to 16,17-splitting to afford the 15-formyl-16,17-seco-16,17-dioic acid 5.Both seco compounds redily undergo lactolone ring closure to give 4a and 6a, respectively.The malonaldehyde moiety of 5 is transformed in two directions: either loss of the formyl group to give 3β-hydroxy-16,17-secoandrost-5-ene-16,17-dioic acid (7a) or decarboxylation to 3β-hydroxy-16-oxo-16,17-secoandrost-5-en-17-oic acid (9) is observed. Key Words: Steroids/ 15-Hydroxymethylene-16-ketosteroids/ D-seco-steroids/ D-Homo-oxa-steroids
