Asymmetric Total Synthesis of Hasubanan Alkaloids: Periglaucines A-C, N,O-Dimethyloxostephine and Oxostephabenine

作者：Ding, Shaolei; Shi, Yingbo; Yang, Baochao; Hou, Min; He, Haibing; Gao, Shuanhu^*

来源：Angewandte Chemie - International Edition, 2023, 62(2).

DOI：10.1002/anie.202214873

• Hasubanan Alkaloids
• Natural Products
• Photoenolization
• Diels-Alder Reaction
• Quaternary Centers
• Total Synthesis

We report herein the asymmetric total synthesis of periglaucines A-C, N,O-dimethyloxostephine and oxostephabenine. The key strategies used include: 1) a Rh-I-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.

• 单位
  5