Total Synthesis of (+)-Malbrancheamide B Employing a Bioinspired Strategy
Abstract
Prenylated indole alkaloids are a class of secondary metabolites isolated from various terrestrial and marine fungi. The common complex structure, featuring a diazabicyclo[2.2.2]octane scaffold fused to a tetrahydrocarbazole unit, and the numerous biological activities make these compounds attractive synthetic targets. In the present work an asymmetric total synthesis of (+)-malbrancheamide B is reported. Key steps are bioinspired diketopiperazine (DKP) assembly, a stereoselective oxidative radical cyclization, which gives access to the three-dimensional bridged diketopiperazine precursor and an intramolecular Friedel-Crafts cyclization providing the hexacyclic skeleton of malbrancheamide B.
Fields of Study & Subjects
Marine Sponges and Natural Products
Synthetic Organic Chemistry Methods
Chemical synthesis and alkaloids
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 10
- Pages
- 3214–3219
- Publication date
- 27 February 2026
- Language
- EN