Synthesis of optically active deacetyl anisomycin

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Abstract
Optically active (−)-deacetyl anisomycin and the enantiomer (+)-deacetyl anisomycin were synthesized starting with (+)-2R 3R tartaric acid. The asymmetric centers of the tartaric acid correspond to the C-2 and C-3 asymmetric centers of anisomycin. N-Benzyl tartarimide (3) was attacked by the Grignard reagent of anisyl chloride followed by lithium aluminium hydride reduction to give two diols (7) and (8) separated by thin-layer chromatography. The diol (8) was debenzylated giving the natural (−)-deacetyl anisomycin. The diol (7) was converted into the epoxide (10) by selective acetylation of the C-4 hydroxy group followed by treatments with phosphorus pentachloride and sodium ethoxide. Opening of the epoxide ring of 10 in boiling acetic acid followed by basic hydrolysis gave (+)-N-benzyl deacetyl anisomycin (11) which was debenzylated to give (+)-deacetyl anisomycin.

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