First stereoselective synthesis of serinol-derived malyngamides and their 1′-epi-isomers |
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| Institution: | 1. Department of Chemistry, University of Lucknow, Lucknow 226007, Uttar Pradesh, India;2. ‘Hygeia’, Center of Excellences in Pharmaceutical Sciences (CEPS), Guru Govind Singh Indraprastha University, Sec 16-C, Dwarka, New Delhi 110078, India;1. Department of Chemistry and Biochemistry, Seton Hall University, 400 South Orange Avenue, South Orange, NJ 07079, United States;2. Department of Chemistry and Biochemistry, Queens College, City University of New York, 65-30 Kissena Blvd., Flushing, NY 11367, United States;1. Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex, France;2. Immunopathologie et Chimie Thérapeutique, Institut de Biologie Moléculaire et Cellulaire CNRS-UPR3572 et FRC 1589, 15 rue Descartes, 67084 Strasbourg Cedex, France;3. Institut Charles Gerhardt UMR 5253 CNRS-UM2-UM1-ENSCM 8, rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France |
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| Abstract: | A stereoselective synthesis of 1a {N-(1R)-2-hydroxy-1-methoxy-methyl ethyl]-(4E,7S)-7-methoxy-4-eicosenamide} has been accomplished in 10 steps from 1-tetradecanol for the first time in 28% overall yield. The key steps involved the coupling reaction of a chiral alkyne with a protected bromide in the presence of t-BuLi, as well as the amidation reaction of (4E,7S)-7-methoxyeicos-4-enoic acid with (R)-methoxyamino alcohol. Acetylation of 1a finished the preparation of 1b {N-(1S)-2-acetyloxy-1-methoxy-methyl ethyl]-(4E,7S)-7-methoxy-4-eicosenamide}. Their 1′-epi-isomers have also been synthesized with a similar strategy. |
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