Synthesis and antifertility activity of zoapatanol analogs

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Abstract
The synthesis of and guinea pig contragestational screening data for several oxepane and 3,8-dioxabicyclo[3,2.1]octane analogs of zoapatanol (1) are described and their structure-activity relationships discussed. Conversion of the 5-keto group on the nonenyl side chain of 1 into a hydroxyl function enhanced the potency. Further significant enhancement in the potency was realized with the transformation of several oxepanes into the 3,8-dioxabicyclo[3.2.1]octane-1-acetic acid derivatives. Detailed, comparative contragestational evaluation of the 3 most potent is presented, which led to the selection of ORF13811 [(1''R,4''S,5''R)-4''-(4",8"-dimethyl-5"-hydroxy-7"-nonenyl)-4''-methyl-3'',8''-dioxabicyclo[3.2.1]octane-1-acetic acid] for further biological evaluation.