A concise and high yielding formal semisynthesis for the marine steroid demethylgorgosterol was developed. Centerpiece was a stereoselective intermolecular cyclopropanation. A variety of demethylgorgosterol analogs were synthesized for biological applications. These include hydrocarbon analogs, diversely functionalized analogs, and fluorophore-steroid conjugates to track and visualize steroids in vivo. Finally, a new method for the synthesis of 3-cyclopropylacrylates was developed. Here, a vinylogous diazoester was utilized to cyclopropanate alkenes. The observed cis-selectivity was explained with π-π-interactions in the transition state.
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