| (S)-(+)-姜黄烯的立体选择性全合成 |
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| 引用本文： | 李安排,李洋,杜振亭,厍学功,潘鑫复. (S)-(+)-姜黄烯的立体选择性全合成[J]. 高等学校化学学报, 2004, 25(5): 862-865 |
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| 作者姓名： | 李安排 李洋 杜振亭 厍学功 潘鑫复 |
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| 作者单位： | 兰州大学化学系, 应用有机化学国家重点实验室, 兰州 730000 |
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| 基金项目： | 国家自然科学基金 (批准号 :2 9972 0 15 )资助 |
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| 摘 要： | 利用不对称双羟化反应和Raney镍的原位还原,高对映选择性和高产率地实现了(S)-(+)-α-姜黄烯(1)的立体选择性合成.用MsCl保护化合物7a和7b时,发现了有趣的消除和重排反应,得到对应的二烯化合物8.
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| 关 键 词： | 防风根烯 倍半萜 (S)-(+)-姜黄烯 立体选择性 非对映体 |
| 文章编号： | 0251-0790(2004)05-0862-04 |
| 收稿时间： | 2002-04-25 |
Stereoselective Total Synthesis of (S)-(+)-α-Curcumene |
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| LI An-Pai,LI Yang,DU Zhen-Ting,SHE Xue-Gong,PAN Xin-Fu. Stereoselective Total Synthesis of (S)-(+)-α-Curcumene[J]. Chemical Research In Chinese Universities, 2004, 25(5): 862-865 |
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| Authors: | LI An-Pai LI Yang DU Zhen-Ting SHE Xue-Gong PAN Xin-Fu |
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| Affiliation: | National Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 73000, China |
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| Abstract: | A facile stereoselective synthetic route to (S)-(+)-α-curcumene 1 was achieved by employing asymmetric dihydroxylation and reduction by Raney Ni in situ. After three steps, the key intermediates 7a and 7b were obtained. They were subjected the to reduction by AlHCl 2 to result in (S)-(+)-α-curcumene (1) in a high enantioselectivity and high yield. In the protective step of compounds 7a and 7b with MsCl in the presence of NEt 3, the elimination reaction and rearrangement were found and the corresponding diene 8 was afforded and elucidated by NMR method. |
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| Keywords: | Bisabolane Sesquiterpene (S)-(+)-α-Curcumene Stereoselectivity Diasteromer |
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