Protecting Groups as Dispersive Directing Groups: Toward the Asymmetric Synthesis of Altemicidin
Abstract
We report progress toward the asymmetric total synthesis of altemicidin, a monoterpene alkaloid featuring a 6-azatetrahydroindane core. A diastereoselective 1,3-dipolar cycloaddition with TMS-diazomethane enabled the construction of a key pyrazoline intermediate. Computational analysis (EDA/NCI) revealed attractive London dispersion forces as the origin of the unexpected stereoselectivity. An effective method to convert the initial silylated 1-pyrazoline into a stable 2-pyrazoline was developed. Selective reductive trifluoroacetylation and SmI 2 -mediated N–N bond cleavage afforded a 1,3-diamine suitable for further functionalization.
Fields of Study & Subjects
Advanced Synthetic Organic Chemistry
Marine Toxins and Detection Methods
Chemical Synthesis and Analysis
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 25
- Pages
- 7959–7964
- Publication date
- 10 June 2026
- Language
- EN