Divergent Total Synthesis of Tacaman Alkaloids: A Skeleton Reorganization Strategy
Abstract
Herein, we present a divergent synthesis of tacaman alkaloids featuring a pivotal pentacyclic intermediate bearing an exocyclic trisubstituted olefin, accessed via a base-promoted intramolecular cyclopropanation/cyclopropane ring-opening/ oxa -Michael cascade and a subsequent electrophilic halomethylation– retro-aza -Michael sequence. This versatile common intermediate enabled the regio- and diastereoselective functionalization of the trisubstituted olefin, affording the total syntheses of tacamonine, tabercamine K, and 19S-hydroxyapotacamine in good yields with excellent stereocontrol. Notably, the Mukaiyama-type hydration reaction was applied to achieve tunable stereochemistry at the C19 and C20 hydroxyl positions.
Fields of Study & Subjects
Synthesis and Characterization of Pyrroles
Marine Sponges and Natural Products
Chemical synthesis and alkaloids
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 6
- Pages
- 2183–2187
- Publication date
- 1 February 2026
- Language
- EN