Synthesis of the tetracyclic core of daphnilactone B-type and yuzurimine-type alkaloids.
The core of daphnilactone B-type and yuzurimine-type alkaloids was synthesized in only 16 steps from a known β-allyl-γ-butyrolactone. The key sequence of Vilsmeier-Haack cyclization and intramolecular azomethine ylide cycloaddition allowed the construction of, in a single step, three of the five rings common to all alkaloids found in both of these classes with perfect chemocontrol.
Département de Chimie, Université de Sherbrooke, 2500 Boulevard de l'Université, Sherbrooke, Québec J1K 2R1, Canada. Guillaume.Belanger@USherbrooke.ca
Guillaume
G
Bélanger
Jonathan
J
Boudreault
François
F
Lévesque
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure
D000470:Alkaloids; C512154:daphnilactone B