A convenient procedure for the synthesis of chiral 6,7-dihydroxy-1-phenylamino-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones |
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| Institution: | 1. Advanced Center for Bioorganic Chemistry of the Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam;2. Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam;3. University of Science and Technology of Hanoi, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam;1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russian Federation;2. Department of Natural Sciences, National Research University – Novosibirsk State University, 630090 Novosibirsk, Russian Federation;3. A. V. Nikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russian Federation;4. V. V. Voevodsky Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russian Federation;5. Department of Physics, National Research University – Novosibirsk State University, 630090 Novosibirsk, Russian Federation;1. State Key Laboratory of Subtropical Silviculture, Zhejiang A&F University, Hangzhou 311300, China;2. Department of Traditional Chinese Medicine, Zhejiang A&F University, Hangzhou 311300, China;3. Centre for Advanced Studies in Botany & Centre for Herbal Sciences, University of Madras, Guindy Campus, Chennai 600 025, Tamil Nadu, India;4. Stem Cell and Molecular Biology Laboratory, Department of Biotechnology, Indian Institute of Technology Madras, Chennai 600036, Tamil Nadu, India;5. Department of Chemistry, Tirunelveli Dakshinamara Nadar Sangam (TDMNS) College, Valliyur, Tirunelveli 627113, Tamil Nadu, India;6. St. Xavier Research Foundation, St. Xavier’s College, High Ground Road, Palayamkottai, Tirunelveli 627002,Tamil Nadu, India;7. Department of Forest Sciences, PB 27 (Latokartanonkaari 7), 00014, University of Helsinki, Finland |
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| Abstract: | The cyclocondensation reactions between l-α-amino acid phenylhydrazides and 2,3-O-isopropylidene-l-erythruronolactone in the presence of a catalytic amount of p-toluenesulfonic acid afforded diastereomerically pure (3S,6R,7R,7aS)-3-substituted-6,7-isopropylidenedioxy-1-phenylamino-dihydro-1H-pyrrolo1,2-a]imidazole-2,5(3H,6H)-diones, which were converted by acidic hydrolysis with MeOH–HCl into their corresponding optically active (3S,6R,7R,7aS)-3-substituted-6,7-dihydroxy-1-phenylamino-dihydro-1H-pyrrolo1,2-a]imidazole-2,5(3H,6H)-diones in good yields. |
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