10.1021/jo00357a023
The research focuses on the highly selective total synthesis of enantiomerically pure (-)-anisomycin, an antibiotic with significant activity against pathogenic protozoa and fungi, which has been used in the treatment of amebic dysentery and trichomonas vaginitis. The study's purpose was to achieve a chiral total synthesis of optically pure (-)-anisomycin through a series of virtually complete regio- and stereocontrolled reactions, without the need for isomer separation. The synthesis began with 4-O-benzyl-2,3-O-bis(methoxymethyl)-L-threose derived from diethyl L-tartrate as the chiral building block and involved several key steps, including a-chelation-controlled addition of hydride, stereospecific cyclization, and selective introduction of the acetyl group with complete regiochemical control. The process utilized various chemicals such as diethyl L-tartrate, 4-methoxybenzyl chloride, benzyl chloroformate, and protecting groups like tert-butyldimethylsilyl and methoxymethyl groups. The successful synthesis was confirmed by comparing the synthesized (-)-anisomycin with authentic samples through melting point, specific optical rotation, and NMR and mass spectrometry analysis, proving 100% enantiomeric purity. The study concluded with the investigation of the antiprotozoal and antifungal activities of the synthetic (-)-anisomycin.
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