Asymmetric Total Synthesis of Hasubanan Alkaloids: Periglaucines A–C, <i>N,O</i>‐Dimethyloxostephine and Oxostephabenine
Shaolei Ding, Yingbo Shi, Baochao Yang, Min Hou, Haibing He, Shuanhu Gao
Abstract
Abstract 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.
Topics & Concepts
Intramolecular forcePropellaneChemistryStereochemistryRing (chemistry)Total synthesisTetrahydrofuranMichael reactionEnantioselective synthesisCatalysisBicyclic moleculeOrganic chemistrySolventTraditional and Medicinal Uses of AnnonaceaeAlkaloids: synthesis and pharmacologyMarine Sponges and Natural Products