Enantioselective synthesis of (R)-incrustoporin,an antibiotic isolated from Incrustoporia carneola |
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| Affiliation: | 1. Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgimento 35, I-56126 Pisa, Italy;2. Corso di Laurea in Scienze Ambientali, Università del Molise, Via Mazzini 8, I-86170 Isernia, Italy;1. Program of Postgraduate in Chemistry, Federal University of Ceará, Pici Campus, Science Center, Fortaleza, CE, CEP: 60455-760, Brazil;2. Federal Institute of Education, Science and Technology of Rio Grande do Norte, Campus Apodi, RN, CEP: 59700-000, Brazil;3. Federal Institute of Education, Science and Technology of Ceará, Campus Acaraú, CE, CEP 62580-000, Brazil;4. University of International Integration Lusofonia Afro-Brasileira – UNILAB, Campus das Auroras, Redenção, CE, CEP: 62790-970, Brazil;1. Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran;2. Pharmaceutical Sciences Research Center, Health Institute, School of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, Iran;1. Department of Biology, Science Faculty, Selcuk University, 42130, Konya, Turkey;2. Department of Molecular Biology and Genetics, Faculty of Engineering and Natural Sciences, Kadir Has University, Istanbul, 34083, Turkey;3. Department of Genetics and Bioengineering, Faculty of Engineering and Architecture, Kastamonu University, Kastamonu, Turkey;4. Department of Range and Watershed Management,Faculty of Water and Soil, University of Zabol, Iran;5. School of Pharmacy, University of Camerino, Via Sant’Agostino 1, I-62032, Camerino, MC, Italy;6. Department of Biotechnology, Science Faculty, Selcuk University, 42130, Konya, Turkey;1. Syngene International Ltd. Biocon Park, Plot 2 & 3, Jigani Link Road, Bangalore, 560099, India;2. Amgen, Inc., 360 Binney Street, Cambridge, MA 02142, United States |
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| Abstract: | Highly enantiomerically enriched (R)-incrustoporin was enantioselectively synthesized in 43.6% overall yield starting from 4-iodotoluene. The key steps of the synthesis included the asymmetric hydrogenation of 1-(p-tolyl)-1-pentyn-3-one catalyzed by a non-racemic Ru(II) complex and the Pd-catalyzed cyclocarbonylation of so-obtained highly enantiomerically enriched 1-(p-tolyl)-1-pentyn-3-ol. This Pd-catalyzed reaction, whose stereochemical outcome was previously unknown, proceeded with retention of configuration and 2.5% or less racemization. The enantiomeric purities of (R)-1-(p-tolyl)-1-pentyn-3-ol and (R)-incrustoporin were evaluated by HPLC analysis on a Chiralcel OJ column as well as by performing the 1H NMR spectra of these compounds in a D2O solution which was saturated with α- or β-cyclodextrin, respectively. |
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