化学
分子内力
亚胺
叠氮化物
全合成
烯烃
还原胺化
立体选择性
对映选择合成
分子内反应
胺气处理
光延反应
试剂
组合化学
药物化学
有机化学
催化作用
作者
Keith P. Reber,Priyansh D. Gujarati
出处
期刊:Synthesis
[Georg Thieme Verlag KG]
日期:2021-11-22
卷期号:54 (05): 1404-1412
被引量:2
标识
DOI:10.1055/s-0041-1737276
摘要
Abstract The enantioselective total synthesis of the alkaloid aristoquinoline has been achieved in seven steps and 26% overall yield. A new preparation of the useful synthetic building block (–)-α-terpinyl amine was also developed in order to avoid stoichiometric mercury reagents or azide-containing intermediates. Key steps in the optimized synthetic route include an intramolecular nitrilium ion cyclization to form the characteristic azabicyclo[3.3.1]nonane ring system and a diastereoselective reduction of the resulting imine mixture to afford the natural product. An isomer of aristoquinoline containing an exocyclic alkene was also obtained and found to exhibit unusual chromatographic and spectroscopic properties.
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