First chiral synthesis of the N-terminal amino acid congener of nikkomycin Z based on lipase-catalyzed enantioselective acetylation of a primary alcohol possessing two stereogenic centers |
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| Institution: | 1. School of Chemistry, Bharathidasan University, Tiruchirappalli 620024, India;2. Department of Chemistry, Texas A&M University, USA;1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, China;2. University of Chinese Academy of Sciences, Beijing 100049, China;1. School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, 6140 Wellington, New Zealand;2. Malaghan Institute of Medical Research, PO Box 7060, Wellington, New Zealand;1. Medicinal Chemistry & Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Department of Pharmaceutical Sciences, Faculty of Science, Utrecht University, PO Box 80082, 3508 TB Utrecht, The Netherlands;2. Membrane Biochemistry and Biophysics, Bijvoet Center for Biomolecular Research, Department of Chemistry, Faculty of Science, Utrecht University, Utrecht, The Netherlands;3. Chemical Biology and Medicinal Chemistry, School of Chemistry, University of Glasgow, Glasgow G12 8QQ, United Kingdom |
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| Abstract: | A stereoselective synthesis of a versatile chiral synthon possessing two stereogenic centers, (2S,3S)-3-2-(5-benzyloxypyridyl)]-2-methyl-1,3-propane diol 12 (>99% ee), was achieved by using a chemo-enzymatic method. The conversion of (2S,3S)-12 to the homochiral intermediate (2S,3S,4S)-2-benzyloxycarbonylamino-4-2-(5-benzyloxypyridyl)]-4-tert-butyldimethylsilyloxy-3-methylbutanoic acid 2 corresponding to the N-terminal amino acid congener of nikkomycin Z 1 is described. |
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