Synthesis of 1,5-diphenylpent-3-en-1-yne derivatives utilizing an aqueous B-alkyl Suzuki cross coupling reaction |
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| Authors: | Da-Wei Chuang Mohamed El-Shazly Chin-Chau Chen Yu-Ming Chung Balaji D. Barve Ming-Jung Wu Fang-Rong Chang Yang-Chang Wu |
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| Affiliation: | 1. Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan;2. Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, Ain-Shams University, Organization of African Unity Street, Abassia, Cairo 11566, Egypt;3. Department of Chemistry, National Sun Yat-sen University, Kaohsiung 804, Taiwan;4. Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan;5. School of Chinese Medicine, College of Chinese Medicine, China Medical University, Taichung 404, Taiwan;6. Natural Medicinal Products Research Center, China Medical University Hospital, Taichung 404, Taiwan;g Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan |
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| Abstract: | 1,5-Diphenylpent-3-en-1-yne derivatives were isolated in minor quantities from terrestrial plants and exhibited strong anti-inflammatory activity. A cross coupling reaction between B-benzyl-9-BBN and chloroenynes under mild condition was developed resulting in the formation of different 1,5-diphenylpent-3-en-1-yne derivatives with a full control on the E/Z selectivity. Several substrates bearing electron-donating and electron-withdrawing substituents were tolerable under the reaction conditions affording the corresponding products in good yields. This is the first study to report the synthesis of a vast array of novel 1,5-diphenylpent-3-en-1-yne derivatives paving the way for the preparation of tailored derivatives on mass scale necessary for biological studies and drug development. |
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| Keywords: | Henna Palladium B-Benzyl-9-BBN B-Alkyl Suzuki coupling Aqueous reaction |
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