A consecutive approach towards the stereoselective synthesis of trisubstituted THF domains |
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| Affiliation: | 1. Division of Medicinal and Process Chemistry, Central Drug Research Institute (CDRI), Lucknow 226 001, India;2. Division of Sophisticated Analytical Instrumentation Facility, Central Drug Research Institute (CDRI), Lucknow 226 001, India;1. Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan;2. Department of Chemistry, University of Yangon, Yangon 11041, Myanmar;3. Faculty of Pharmacy, Hasanuddin University, Makassar 90245, South Sulawesi, Indonesia;4. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan;5. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan;1. Bristol-Myers Squibb, Drug Discovery, Wallingford, CT 06492, USA;2. Bristol-Myers Squibb, Drug Product Science & Technology, Princeton, NJ 08543, USA |
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| Abstract: | A highly efficient, consecutive approach for the construction of synthetically valued, enantiomerically pure, trisubstituted THF domains 3–10 in a stereoselective manner starting from glycal derived allylic alcohols 1a–1d under Sharpless asymmetric epoxidation (SAE) conditions is reported. The reaction involves the intramolecular asymmetric ring opening (ARO) of in situ formed enantiopure 2,3-epoxy alcohols followed by protection of the diol. |
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