Total synthesis of (+)- and (-)-neopyrrolomycins, chlorinated phenylpyrrole antibiotics

Article abstract of DOI:10.1246/bcsj.67.1449

The first total synthesis of (+)- and (-)-neopyrrolomycins (11a and 11b) is detailed based on regioselective chlorinations of 3,5-dichloroanisole (2) and 1-(2,3,4-trichloro-6-methoxyphenyl)-1H-pyrrole-2-carboxylic acid (8) with isocyanuric trichloride, followed by optical resolution of racemic neopyrrolomycin (11) with N-(p-tolylsulfonyl)-L-phenylalanyl chloride. Several analogs (21-25) have been prepared from the intermediates, and the structure-activity relationships are also discussed.