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Abstract A formal semisynthesis of the marine steroid demethylgorgosterol was realized by the synthesis of an advanced ketone intermediate. The intermediate was synthesized in ten steps, starting from commercially available stigmasterol. An overall yield of 27 % was achieved. The key step was a stereoselective cyclopropanation reaction with 82 % yield, a trans/cis ratio of 89 : 11, and drtrans of >99 : 1.
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