Synthesis of optically active 1,3-dioxin-4-one derivatives having a hydroxymethyl group at the 2-position and their use for regio-, diastereo-, and enantioselective synthesis of substituted cyclobutanols |
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| Institution: | 1. Process Development Laboratories, Sankyo Co., Ltd., 1-12-1 Shinomiya, Hiratsuka 254-8560, Japan;2. Medicinal Chemistry Department, Discovery Research Laboratory, Tanabe Seiyaku Co., Ltd., 2-2-5-Kawagishi, Toda 335-8505, Japan;3. Emeritus Professor of Tohoku and Kanazawa Universities, 2-35-19 Yagiyama-Honcho, Taihaku-ku, Sendai 982-0801, Japan;4. School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan;1. School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng 224051, China;2. Residues and Resource Reclamation Centre, Nanyang Environment and Water Research Institute, Nanyang Technological University, 1 Cleantech Loop, Singapore 637141, Singapore;1. Medicinal Chemistry Department, PharmaMar S.A., Pol. Ind. La Mina Norte, Avenida de los Reyes 1, 28770 Colmenar Viejo (Madrid), Spain;2. Departamento de Química Fundamental, Facultade de Ciencias e Centro de Investigacións Científicas Avanzadas (CICA), Universidade da Coruña, 15071 A Coruña, Spain |
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| Abstract: | A new method for preparing optically active 1,3-dioxin-4-one derivatives is presented. A series of prochiral 2,2-bis(hydroxymethyl)-1,3-dioxin-4-ones was synthesized by 4+2]cycloaddition of acylketene to protected 1,3-dihydroxy-2-propanone derivatives followed by deprotection of the hydroxyl groups. Desymmetrization of the prochiral dioxinones by lipase-catalyzed monoacetylation afforded optically active 2-(hydroxymethyl)dioxinones. Intramolecular photo2+2]cycloaddition of ω-alkenyl esters of these alcohols provided an efficient method for regio-, diastereo-, and enantioselective synthesis of cyclobutanols. |
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