Synthesis of 3-benzyloxyl-17-maleyloxy-16, 17-secoestra- 1, 3, 5 (10)-triene-16-nitrile - Sinteza 3-benziloksi-17-maleiloksi- 16, 17-sekoestra-1, 3, 5 (10)-trien-16-nitrila

Abstract

Under the conditions of Beckmann fragmentation reaction 3-benzyloxy-17(-hydroxyestra-1, 3, 5, (10)-triene-16-one oxime (2) gave the D-seco derivative 3. Sodium borohydride reduction of this compound afforded 3-benzyloxy-17-hydroxy-16, 17-secoestra-1, 3, 5 (10)-triene-16-nitrile (4). The esterification of seco-cyanoalcohol 4 was achieved by action of maleic acid anhydride in dry pyridine, yielding 3-benzyloxy-17-maleyloxy-16 17-secoestra-1, 3, 5 (10)-triene-16-nitrile (5).

Keywords

• steroids
• 16,17-seco-estrone derivatives
• synthesis
• Beckmann fragmentation
• reaction
• esterification
• hemiesters