| A Concise Synthesis of (－)-Indolizidines 209D and 209B |
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| 引用本文： | WU Hao,YU Menglong,ZHANG Yazhu,ZHAO Gang. A Concise Synthesis of (－)-Indolizidines 209D and 209B[J]. 中国化学, 2009, 27(1): 183-188. DOI: 10.1002/cjoc.200990015 |
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| 作者姓名： | WU Hao YU Menglong ZHANG Yazhu ZHAO Gang |
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| 作者单位： | Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, ; Chinese Academy of Sciences, Shanghai 200032, China ; |
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| 摘 要： | A general stereoselective synthetic route to 5-substituted and 5,8-disubstituted indolizidine alkaloids has been developed starting from commercially available L-proline. (－)-Indolizidines 209D and 209B were efficiently synthesized in 9.8% and 14.8% overall yields in seven and five-step reactions from readily available aldehyde 3 and ketone 10, respectively. The key steps of this synthesis involve a substrate-induced asymmetric addition of ethyl lithiopropiolate to aldehyde 3 or methyl ketone 10, and a two-step one-pot hydrogenation/cyclization sequence to construct the bicyclic skeleton.
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| 关 键 词： | synthesis indolizidine alkaloid |
| 收稿时间： | 2008-11-05 |
| 修稿时间： | 2008-12-08 |
A Concise Synthesis of (-)-Indolizidines 209D and 209B |
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| WU Hao,YU Menglong,ZHANG Yazhu,ZHAO Gang. A Concise Synthesis of (-)-Indolizidines 209D and 209B[J]. Chinese Journal of Chemistry, 2009, 27(1): 183-188. DOI: 10.1002/cjoc.200990015 |
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| Authors: | WU Hao YU Menglong ZHANG Yazhu ZHAO Gang |
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| Affiliation: | 1. Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;2. Tel.: 0086‐021‐54925182;3. Fax: 0086‐021‐64166128 |
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| Abstract: | A general stereoselective synthetic route to 5‐substituted and 5,8‐disubstituted indolizidine alkaloids has been developed starting from commercially available L‐proline. (?)‐Indolizidines 209D and 209B were efficiently synthesized in 9.8% and 14.8% overall yields in seven and five‐step reactions from readily available aldehyde 3 and ketone 10 , respectively. The key steps of this synthesis involve a substrate‐induced asymmetric addition of ethyl lithiopropiolate to aldehyde 3 or methyl ketone 10 , and a two‐step one‐pot hydrogenation/cyclization sequence to construct the bicyclic skeleton. |
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| Keywords: | synthesis indolizidine alkaloid |
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