烯烃烯化和芳基化的构筑以及石松科生物碱的全合成研究
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摘要
本论文分为两部分,第一部分介绍了基于烯丙醇的semipinacol重排／Grob碎裂化反应进行烯烃烯化以及芳基化反应的研究；第二部分介绍了我们组对石松科生物碱Sieboldine A以及Fawcettimine的全合成研究。
第一部分：通过NBS参与的烯丙醇的semipinacol重排反应以及NaOH促进的Grob碎裂化反应,我们建立了立体选择性烯烃烯化以及芳基化反应的方法。该方法不需要过渡金属的催化,反应体系不需要特别的除水除氧,同时反应操作简单,条件温和。进一步研究提出了针对开环底物以及环状底物不同的反应机理。
第二部分：石松科生物碱(Lycopodium alkaloids)是一类结构相似,具有喹嗪,吡啶或者α-吡啶酮类型相同生源的一类天然生物碱。针对其中的Sieboldine A以及Fawcettimine天然产物,我们利用本组新发表的构筑手性螺醚以及手性季碳的方法对他们的合成进行了初步的探索。虽然碰到了很多困难,但是这些努力为以后该类天然产物的合成积累了一定的经验。
The thesis aims at the studies "Arylation and Vinylation of Alkenes Based on Unusual Sequential Semipinacol Rearrangement/Grob Fragmentation of Allylic Alco-hols and the total synthesis of Sieboldine A and Fawcettimine of Lycopodium alkaloids" and includes two parts:
Part I:Alkenes can be stereoselectively arylated and vinylated without transition-metal catalyst under mild conditions through an interesting NBS-promoted semipinacol rearrangement and a subsequent unusual NaOH-mediated Grob fragmentation. The current protocol is insensitive to oxygen and moisture, leading to a very convenient experimental manipulation. And, we gave two different reaction mechanisms for cyclic and acyclic substrates respectively.
Part II:Lycopodium alkaloids are a structurally related, quinolizine and pyridine or a-pyridone type, and originally identified from Lycopodium. Initially, we aimed at the synthesis of Sieboldine A and Fawcettimine of Lycopodium alkaloids based on our own reaction methods which were "Synthesis of Chiral Spiroethers" and "Construction of Chiral All-Carbon Quaternary Stereocenters in Spirocyclic". Although many efforts have been made, we do not complete the total synthesis. But all those endeavors have afforded valuable information for the following investigations.
第一部分：通过NBS参与的烯丙醇的semipinacol重排反应以及NaOH促进的Grob碎裂化反应,我们建立了立体选择性烯烃烯化以及芳基化反应的方法。该方法不需要过渡金属的催化,反应体系不需要特别的除水除氧,同时反应操作简单,条件温和。进一步研究提出了针对开环底物以及环状底物不同的反应机理。
第二部分：石松科生物碱(Lycopodium alkaloids)是一类结构相似,具有喹嗪,吡啶或者α-吡啶酮类型相同生源的一类天然生物碱。针对其中的Sieboldine A以及Fawcettimine天然产物,我们利用本组新发表的构筑手性螺醚以及手性季碳的方法对他们的合成进行了初步的探索。虽然碰到了很多困难,但是这些努力为以后该类天然产物的合成积累了一定的经验。
The thesis aims at the studies "Arylation and Vinylation of Alkenes Based on Unusual Sequential Semipinacol Rearrangement/Grob Fragmentation of Allylic Alco-hols and the total synthesis of Sieboldine A and Fawcettimine of Lycopodium alkaloids" and includes two parts:
Part I:Alkenes can be stereoselectively arylated and vinylated without transition-metal catalyst under mild conditions through an interesting NBS-promoted semipinacol rearrangement and a subsequent unusual NaOH-mediated Grob fragmentation. The current protocol is insensitive to oxygen and moisture, leading to a very convenient experimental manipulation. And, we gave two different reaction mechanisms for cyclic and acyclic substrates respectively.
Part II:Lycopodium alkaloids are a structurally related, quinolizine and pyridine or a-pyridone type, and originally identified from Lycopodium. Initially, we aimed at the synthesis of Sieboldine A and Fawcettimine of Lycopodium alkaloids based on our own reaction methods which were "Synthesis of Chiral Spiroethers" and "Construction of Chiral All-Carbon Quaternary Stereocenters in Spirocyclic". Although many efforts have been made, we do not complete the total synthesis. But all those endeavors have afforded valuable information for the following investigations.
引文
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