Synthesis of 7,9-dideoxybaccatin IV analogs from sinenxan A |
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Authors: | Meng Zhang Ji-Yu Guo Xiao-Tian Liang |
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Affiliation: | Institute of Materia Medica, Chinese Academy of Medical Science and Peking Union Medical College, Beijing 100050, People's Republic of China |
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Abstract: | Sinenxan A, a taxoid isolated from callus tissue cultures of Taxus yunnanensis was converted into 13-oxo-7,9-dideoxy-2-debenzoyl-2-acetyl-baccatin IV and 7,9-dideoxy-2-debenzoyl-4-deacetyl-baccatin IV, a key framework of 1,7,9-trideoxypaclitaxel. Several special steps in this transformation are worthy of note: (1) deoxygenation by treatment with hypophosphorous acid at C-14 position; (2) a highly regioselective O-deacetylation of taxanes at C-5 position; and (3) stereoselective reduction of the 13-carbonyl group by transannular assistance from the C-4-hydroxyl. |
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Keywords: | Sinenxan A Deoxygenation Paclitaxel |
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