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- Title
Asymmetric Total Synthesis of Hasubanan Alkaloids: Periglaucines A–C, N,O‐Dimethyloxostephine and Oxostephabenine.
- Authors
Ding, Shaolei; Shi, Yingbo; Yang, Baochao; Hou, Min; He, Haibing; Gao, Shuanhu
- Abstract
We report herein the asymmetric total synthesis of periglaucines A–C, N,O‐dimethyloxostephine and oxostephabenine. The key strategies used include: 1) a RhI‐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.
- Subjects
ASYMMETRIC synthesis; TETRAHYDROFURAN; NATURAL products; ALKALOIDS
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 2, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202214873