Stereoselective construction of skipped polyol enabled by oxonia-Cope rearrangement and iodolactonization： enantioselective synthesis of （＋）-yashabushitriol
Skipped polyol is a common motif in numerous biologically significant polyketides and has been the focus of the development of novel synthetic methods and strategies. In this work, we devised a highly diastereoselective approach to access skipped triol （anti, syn-isomer） from a chiral α-allenic alco...
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| Veröffentlicht in: | Science China. Chemistry 2016-09, Vol.59 (9), p.1197-1204 |
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| container_issue | 9 |
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| container_title | Science China. Chemistry |
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| creator | He, Guoli Wang, Yan Lai, Calvine Li, Wenhua Hong, Ran |
| description | Skipped polyol is a common motif in numerous biologically significant polyketides and has been the focus of the development of novel synthetic methods and strategies. In this work, we devised a highly diastereoselective approach to access skipped triol （anti, syn-isomer） from a chiral α-allenic alcohol which was derived from kinetic resolution in our previous studies. An iodolactonization and subsequent radical deiodonation efficiently introduced the hydroxyl group at C3 in a highly diastereoselective manner and exemplified in enantioselective total synthesis of （＋）-yashabushitriol. |
| doi_str_mv | 10.1007/s11426-016-0073-3 |
| format | Article |
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| subjects | Chemistry Chemistry and Materials Science Chemistry/Food Science Cope重排 Enantiomers Hydroxyl groups Stereoselectivity Synthesis 不对称全合成 不对称合成 启用 多元醇 碘内酯化反应 立体选择性 聚酮化合物 |
| title | Stereoselective construction of skipped polyol enabled by oxonia-Cope rearrangement and iodolactonization： enantioselective synthesis of （＋）-yashabushitriol |
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