A chemoenzymatic synthesis of both enantiomers of a cis-lignan lactone |
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| Affiliation: | 1. Department of Pharmacognosy and Utilization Key Laboratory of Northeast Plant Materials, School of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang 110016, China;2. Division of Physical Sciences and Engineering, King Abdullah University of Science and Technology (KAUST), Thuwal, Saudi Arabia;1. Modern Research Center for Traditional Chinese Medicine, Beijing University of Chinese Medicine, Beijing 100029, People''s Republic of China;2. School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100102, People''s Republic of China;3. Department of Medicinal Chemistry, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, People''s Republic of China;1. Department of Interdisciplinary Program in Biomedical Science Major, Soonchunhyang Graduate School, Bucheon, Gyeonggi-do 420-767, Republic of Korea;2. Department of Internal Medicine, Soonchunhyang University Gumi Hospital, Gumi, Gyeongsangbuk-do 39371, Republic of Korea;3. Division of Allergy and Respiratory Disease, Soonchunhyang University Bucheon Hospital, 1174 Jung-dong, Bucheon, Gyeonggi-do 420-767, Republic of Korea;4. Laboratory of Cytokine Immunology, Department of Biomedical Science and Technology, Konkuk University, 120 Neungdong-ro, Seoul 143-701, Republic of Korea;5. Division of Respiratory Disease, Soonchunhyang University Seoul Hospital, YongSan-gu, Seoul 04401, Republic of Korea |
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| Abstract: | The stereoselective acetylation of meso-2,3-bis(3,4-dimethoxybenzyl)butanediol by vinyl acetate in the presence of Candida antarctica lipase in benzene gave the corresponding (+)-(2S,3R) monoester (ee ≥98%). Transesterification of meso-2,3-bis(3,4-dimethoxybenzyl)butyl diacetate, in the presence of the same enzyme, by ethanol in benzene/isopropyl ether gave the corresponding (−)-(2R,3S) monoester (ee ≥98%). Both enantiomers of the known cis-2,3-bis(3,4-dimethoxybenzyl)butyrolactone were synthesized from these monoesters. |
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