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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.
Abstract After more than 70 years since their discovery, Criegee intermediates (CIs) are back at the forefront of modern chemistry of short‐lived reactive intermediates. They play an important role in the mechanistic context of chemical synthesis, total synthesis, pharmaceuticals, and, most importantly, climate‐controlling aerosol formation as well as atmospheric chemistry.
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