Enantioselective Synthesis and Antimicrobial Activities of Tetrahydro‐Β‐Carboline Diketopiperazines |
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| Authors: | Yangmin Ma Hao Wu Jin Zhang Yanchao Li |
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| Affiliation: | 1. Key Laboratory of Auxiliary Chemistry and Technology for Chemical Industry, Ministry of Education, Shaanxi University of Science & Technology, , Xi'an, China;2. Northwest Institute of Nonferrous Metals, , Xi′an, China |
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| Abstract: | A series of single isomers tetrahydro‐β‐carboline diketopiperazines were stereoselectively synthesized starting from l ‐tryptophan methyl ester hydrochloride and six aldehydes through a four‐step reaction including Pictet‐Spengler reaction, crystallization‐induced asymmetric transformations (CIAT), Schotten‐Baumann reaction, and intramolecular ester amidation. The chemical structures were characterized by nuclear magnetic resonance (NMR) and elemental analysis, among which two compounds were determined by x‐ray single crystal diffraction. Moreover, antimicrobial activities of all the compounds were also tested. Chirality 25:656–662, 2013. © 2013 Wiley Periodicals, Inc. |
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| Keywords: | antimicrobial activity configuration crystallization‐induced asymmetric transformations tetrahydro‐β ‐carboline diketopiperazine x‐ray single crystal diffraction |
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