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A concise asymmetric total synthesis of (+)-fawcettimine
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2020-08-28 , DOI: 10.1016/j.tetlet.2020.152329 Xin Zeng , Zhuqing Jia , Fayang G. Qiu
中文翻译:
简明的不对称全合成(+)-法西替明
更新日期:2020-09-20
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2020-08-28 , DOI: 10.1016/j.tetlet.2020.152329 Xin Zeng , Zhuqing Jia , Fayang G. Qiu
A straightforward and stereocontrolled total synthesis of (+)-fawcettimine was accomplished from the known (R)-5-methyl-2-cyclohexen-one in 11 steps. The synthesis features a palladium mediated cycloalkenylation of a silyl enol ether for assembling the 6/5-hydrindane system and generating a quaternary carbon center in one step; an oxa-Diels-Alder reaction followed by a Mitsunobu reaction to construct the Heathecock intermediate, i.e., the 6–5-9 tricycle skeleton.
中文翻译:
简明的不对称全合成(+)-法西替明
通过已知的(R)-5-甲基-2-环己烯酮以11个步骤完成(+)-法西替明的直接和立体控制的总合成。该合成的特征是钯介导的甲硅烷基烯醇醚的环烯基化反应,可用于组装6 / 5-茚满体系并一步生成一个季碳中心。先进行oxa-Diels-Alder反应,然后进行Mitsunobu反应,以构建Heathecock中间体,即6-5-9三轮车骨架。