18d-Glycyrrhetic acid (lb) was converted in good yield to the 3-oxo-4,4-bis(nor-18J-olean-4-ene) derivative 11a in 25% overall yield. Derivatives of lb substituted in the A, B, C, and E ring were also prepared. Several 11-deoxoglycyrrhetic acid derivatives exhibited anti-DCA activity. In particular, when administered subcutaneously, 3-oxo-18/3-olean-12-en-30-oic acid (2d) had about 75% the activity of spironolactone administered subcutaneously. Several compounds also exhibited weak antiviral and antiinflammatory properties.
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