天然产物Dasyscyphin D和E，Mitchellene B的全合成研究及手性膦酸催化的不对称Robinson环化反应研究
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摘要
本论文对二萜类天然产物Dasyscyphin D和E,倍半萜类天然产物MitchelleneB进行了全合成研究,同时对手性膦酸催化的不对称Robinson环化反应进行了方法学研究。
第一章具有生理活性的二萜类天然产物的合成进展(综述)
本综述根据碳骨架的环系类型将二萜分为链状二萜,双环二萜,三环二萜,四环二萜和大环二萜,以此为基础分别举例论述了一些具有重要生理活性的二萜化合物的合成进展。并列举了本组对二萜类天然产物的全合成工作。
第二章Dasyscyphin D和E全合成研究
简要介绍了具有特殊的[6-5-6-6]四环骨架的二萜类天然产物的分离、生理活性及合成进展,并阐述了三种不同的合成策略对二萜类天然产物Dasyscyphin D和E进行全合成研究。采用PtCl2催化的环戊烷化反应构建分子骨架中的B环,以两次Robinson环化反应构建分子骨架中的C、D环,以9步22.6%的总产率完成了天然产物Dasyscyphin D的全合成。
第三章手性膦酸催化的不对称Robinson环化反应
简要介绍了手性膦酸催化的不对称反应以及Robinson环化反应。以2-茚酮和1-氯-3-戊酮为反应底物,采用不同的手性膦酸为催化剂进行不对称Robinson环化反应。该方法学具有反应底物简单易得、条件温和、高区域选择性等优点。
第四章Mitchellene B的合成研究
简要介绍了倍半萜类天然产物Mitchellene B的分离及生理活性。初步尝试了利用多样性导向的全合成策略,对倍半萜类天然产物Mitchellene B进行合成研究：应用Hajos-Parrish反应、Pauson-Khand反应为关键反应。
This thesis mainly focused on the total synthesis of dipertene-type nature product: Dasyscyphin D. Meanwhile, syntheses of Dasyscyphin E and Mitchellene B were also studied. And asymmetric Robinson annulation catalyzed by the chiral phosphoric acid was studied. This thesis consists of the following four chapters:
Chapter1. Total syntheses of dipertene-type nature products.(review)
In this review, based on the type of the skeletons of the diterpenoids, we divided the diterpenoids into chain diterpenoids, bicyclic diterpenoids, tricyclic diterpenoids, tetracyclic diterpenoids and macrocyclic diterpenoids. On this basis, We listed some total syntheses of the diterpenoids which have important physiological activities. And we cited the total syntheses of diterpenoid natural products in our group.
Chapter2. Total syntheses of dasyscyphin D and E
Three synthetic strategies toward the syntheses of the terpenoids natural products Dasyscyphin D and E were proposed. Finally, the first, concise and efficient total synthesis of (±)-Dasyscyphin D was acomplished by the third strategy in9steps with22.6%overall yield. The key steps involved PtCl2-catalyzed pentannulation reaction and double acid catalyzed Robinson annulations.
Chapter3. Asymmetric Robinson annulation catalyzed by chiral phosphoric acid
Studies on the asymmetric Robinson annulation catalyzed by the chiral phosphoric acid were demonstrated. This methodology used2-indanones and1-chloro-3-pentanone as the substraties, and a varieties of chiral phosphoric acids were prepared as the catalysts.
Chapter4. Studies on the synthesis of mitchellene B
Studies on the synthesis of mitchellene B were demonstrated. The key steps involved Hajos-Parrish reaction and Pauson-Khand reaction. We had carried out a series of attempts of the choice of the promoters in the Pauson-Khand reaction. This synthetic efforts will pave the way for the total synthesis of mitchellene B.
第一章具有生理活性的二萜类天然产物的合成进展(综述)
本综述根据碳骨架的环系类型将二萜分为链状二萜,双环二萜,三环二萜,四环二萜和大环二萜,以此为基础分别举例论述了一些具有重要生理活性的二萜化合物的合成进展。并列举了本组对二萜类天然产物的全合成工作。
第二章Dasyscyphin D和E全合成研究
简要介绍了具有特殊的[6-5-6-6]四环骨架的二萜类天然产物的分离、生理活性及合成进展,并阐述了三种不同的合成策略对二萜类天然产物Dasyscyphin D和E进行全合成研究。采用PtCl2催化的环戊烷化反应构建分子骨架中的B环,以两次Robinson环化反应构建分子骨架中的C、D环,以9步22.6%的总产率完成了天然产物Dasyscyphin D的全合成。
第三章手性膦酸催化的不对称Robinson环化反应
简要介绍了手性膦酸催化的不对称反应以及Robinson环化反应。以2-茚酮和1-氯-3-戊酮为反应底物,采用不同的手性膦酸为催化剂进行不对称Robinson环化反应。该方法学具有反应底物简单易得、条件温和、高区域选择性等优点。
第四章Mitchellene B的合成研究
简要介绍了倍半萜类天然产物Mitchellene B的分离及生理活性。初步尝试了利用多样性导向的全合成策略,对倍半萜类天然产物Mitchellene B进行合成研究：应用Hajos-Parrish反应、Pauson-Khand反应为关键反应。
This thesis mainly focused on the total synthesis of dipertene-type nature product: Dasyscyphin D. Meanwhile, syntheses of Dasyscyphin E and Mitchellene B were also studied. And asymmetric Robinson annulation catalyzed by the chiral phosphoric acid was studied. This thesis consists of the following four chapters:
Chapter1. Total syntheses of dipertene-type nature products.(review)
In this review, based on the type of the skeletons of the diterpenoids, we divided the diterpenoids into chain diterpenoids, bicyclic diterpenoids, tricyclic diterpenoids, tetracyclic diterpenoids and macrocyclic diterpenoids. On this basis, We listed some total syntheses of the diterpenoids which have important physiological activities. And we cited the total syntheses of diterpenoid natural products in our group.
Chapter2. Total syntheses of dasyscyphin D and E
Three synthetic strategies toward the syntheses of the terpenoids natural products Dasyscyphin D and E were proposed. Finally, the first, concise and efficient total synthesis of (±)-Dasyscyphin D was acomplished by the third strategy in9steps with22.6%overall yield. The key steps involved PtCl2-catalyzed pentannulation reaction and double acid catalyzed Robinson annulations.
Chapter3. Asymmetric Robinson annulation catalyzed by chiral phosphoric acid
Studies on the asymmetric Robinson annulation catalyzed by the chiral phosphoric acid were demonstrated. This methodology used2-indanones and1-chloro-3-pentanone as the substraties, and a varieties of chiral phosphoric acids were prepared as the catalysts.
Chapter4. Studies on the synthesis of mitchellene B
Studies on the synthesis of mitchellene B were demonstrated. The key steps involved Hajos-Parrish reaction and Pauson-Khand reaction. We had carried out a series of attempts of the choice of the promoters in the Pauson-Khand reaction. This synthetic efforts will pave the way for the total synthesis of mitchellene B.
引文
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