Construction of a Chasmanine Skeleton Enabled by Hg(OAc)2-Promoted Vinylogous Mannich Reaction
Abstract
Chasmanine and puberuline C share a hexacyclic ABCDEF-ring but differ in the fusion pattern of their 5- and 6-membered F-rings. Here, we present a novel strategy for constructing the chasmanine skeleton, starting from a key intermediate employed in our total synthesis of puberuline C. Following optimization of a radical cyclization to build the ABCE-ring system, Hg(OAc)2-promoted vinylogous Mannich and Mukaiyama aldol reactions formed the F- and D-rings, respectively, thereby completing the assembly of the hexacycle.
Fields of Study & Subjects
Advanced Synthetic Organic Chemistry
Catalytic C–H Functionalization Methods
Synthetic Organic Chemistry Methods
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 30
- Pages
- 9817–9822
- Publication date
- 20 July 2026
- Language
- EN