Complete synthesis of the antibiotic anisomycin

The synthesis of the antibiotic anisomycin ( 1 ) is described. In the key step 3, 4-dimethoxy-thiopyrrolidone ( 16 ), prepared from diethyl L -( + )-tartarate ( 4 ) was converted to the thioiminoester 18 , which upon treatment with trimethylphosphite yielded the benzylidene derivative 19 . Cleavage of the ester group of 19 and hydrogenation of the decarboxylation product gave the two isomers 21 and 22 . 22 was converted into desacetylanisomycin ( 3 ) and anisomycin ( 1 ).