Hasubanan 生物碱的非对映体全合成：佩里格鲁辛 A-C、N,O-二甲氧基氧化石蒜碱和氧化石蒜苯乙胺。
Asymmetric Total Synthesis of Hasubanan Alkaloids: Periglaucines A-C, N,O-Dimethyloxostephine and Oxostephabenine.
机构信息
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N Zhongshan Road, Shanghai, 200062, China.
College of Chemistry and Materials Science, Sichuan Normal University, 5 Jingan Road, Chengdu, 610068, China.
出版信息
Angew Chem Int Ed Engl. 2023 Jan 9;62(2):e202214873. doi: 10.1002/anie.202214873. Epub 2022 Dec 2.
We report herein the asymmetric total synthesis of periglaucines A-C, N,O-dimethyloxostephine and oxostephabenine. The key strategies used include: 1) a Rh -catalyzed regio- and diastereoselective Hayashi-Miyaura reaction to connect two necessary fragments; 2) an intramolecular photoenolization/Diels-Alder (PEDA) reaction to construct the highly functionalized tricyclic core skeleton bearing a quaternary center; 3) a bio-inspired intramolecular Michael addition and transannular acetalization to generate the aza[4.4.3]propellane and the tetrahydrofuran ring.
我们在此报告了吡咯里西啶生物碱类化合物 A-C、N,O-二甲氧基氧化石蒜碱和氧化石蒜贝宁的非对映体全合成。所采用的关键策略包括：1）铑催化的区域和立体选择性 Hayashi-Miyaura 反应连接两个必要的片段；2）分子内光致烯醇化/Diels-Alder（PEDA）反应构建带有季碳原子的高度官能化的三环核心骨架；3）受生物启发的分子内迈克尔加成和环间缩醛化生成氮杂[4.4.3]螺环丙烷和四氢呋喃环。
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