SYNTHESIS OF STEROIDAL AND TERPENOIDAL EXTRANUCLEO THIAZOLIDINONES

3-Oxo-5-beta-cholan-24-oic-acid (1a), 3-oxo-lanost-8,24-diene (2a) and 3-oxo-olean-12-ene (3a) on reaction with hydrazine hydrate In alcoholic solution gave the respective 3-hydrazones (1b, 2b and 3b). Subsequent reaction of these 3-hydrazones with ammonium thiocyanate in benzene solution afforded 3-thiosemicarbazone derivatives (1c, 2c and 3c) which undergo cyclisation with chloroacetic acid in the presence of anhydrous sodium acetate to yield 3-14'-oxo-1',3'-thiazolidin-2'-ylidine hydrazino]-5-beta-cholan-24-oic acid (1d), 3-[4'-oxo-1',3'-thiazolidin-2'-ylidine-hydrazino]lanost-8,24-diene (2d) and 3-14'-oxo-1', 3'-thiazolidin-2'-ylidine-hydrazino] olean-12-ene (3d), respectively.