Asymmetric synthesis of triepoxyzerumbol |
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| Institution: | 1. Department of Advanced Bioscience, Graduate School of Agriculture, Kinki University, Nara 631-8505, Japan;2. Graduate School of Advanced Life Science and Technology, Hokkaido University, N21, W11 Sapporo 001-0021, Japan;3. Nagahama Institute of Bio-Science and Technology, Nagahama, Shiga 526-0829, Japan;4. Kyoto University of Education, Fushimi, Kyoto 612-8522, Japan |
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| Abstract: | The achiral sesquiterpene zerumbone 1, which is readily available from wild ginger, has a unique functionality and reactivity making it a convenient starting material for its conversion into useful compounds, such as paclitaxel. Optically active triepoxyzerumbol (?)-3 and its acetate (+)-4 were synthesized by lipase-catalyzed enantioselective transesterification of racemic 3. Under optimized conditions, a lipase from Alcaligenes sp. (Meito QL) catalyzed the reaction of racemic 3 with isopropenyl acetate in THF at 35 °C to afford (1S)-3 and (1R)-4 with an E-value of 79. The absolute configuration of (1R)-4 was determined by single crystal X-ray diffraction of its ester with a chlorine atom using the anomalous dispersion effect. |
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