Diastereoselective synthesis of a novel lactam peptidomimetic exploiting vinylogous Mannich addition of 2-silyloxyfuran reagents |
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| Institution: | 1. Dipartimento Farmaceutico dell''Università, Viale delle Scienze, I-43100 Parma, Italy;2. Istituto per l''Applicazione delle Tecniche Chimiche Avanzate ai Problemi Agrobiologici del CNR, Via Vienna 2, I-07100 Sassari, Italy;3. Dipartimento di Chimica dell''Università, Via Vienna 2, I-07100 Sassari, Italy;1. Department of Chemistry, University of Delhi, North Campus, Delhi, 110007, India;2. Department of Chemistry, MNIT, Jaipur, Rajasthan, 302017, India;3. Department of Chemistry, University of Lucknow, Lucknow, Uttar Pradesh, 226007, India;1. School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran;2. Chemistry Department, Zhejiang University, Hangzhou 310027, PR China;1. Department of Biomolecular Science, Section of Organic Chemistry and Organic Natural Compounds, Università degli Studi di Urbino “Carlo Bo”, Via I Maggetti 24, 61029 Urbino, Italy;2. Department of Chemistry, Università degli Studi di Siena, Via Aldo Moro, 53100 Siena, Italy;1. School of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, Japan;2. Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan;3. Faculty of Pharmaceutical Sciences, Hokuriku University, Ho-3 Kanagawa-machi, Kanazawa 920-1181, Japan |
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| Abstract: | The total synthesis of a potential inhibitor of HIV-protease—the chiral nonracemic six-membered hydroxy lactam 6—has been accomplished, that involves, as key reaction, the highly diastereoselective vinylogous Mannich addition of furan-based silyloxy diene 7 to glyceraldeyde imine 8. |
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