Total synthesis of anisomycin

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Abstract
Two synthetic approaches to anisomycin had been studied. One approach used 2R 3R tartaric acid as starting material and was successfully converted to the hydrochlorides of (+)-anisomycin (22) in an overall yield of about 5% and (−)-anisomycin (1) in about 1% yield. Liberation of the free bases gave (+)-anisomycin and (−)-anisomycin. The other approach started with α-anisyl pyrrole and was converted to (±)-deacetyl anisomycin 2. The conversion of 2 to anisomycin was done by treating natural deacetyl anisomycin with benzyl bromide to give 9. Conversion of 8 and 9 to (+)-anisomycin and (−)-anisomycin was done by selective acetylation with acetic anhydride and debenzylation under hydrogenation condition.

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