Bulletin of the Chemical Society of Japan

Total Synthesis of (+)-and (-)-Neopyrrolomycins, Chlorinated Phenylpyrrole Antibiotics.

K Tatsuta, M Itoh

Index: Tatsuta; Itoh Bulletin of the Chemical Society of Japan, 1994 , vol. 67, # 5 p. 1449 - 1455

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Citation Number: 5

Abstract

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 ...