Enantioselective total synthesis of (-)-lansai B and (+)-nocardioazines A and B.
The concise total syntheses of the bis(pyrroloindolines) (-)-lansai B and (+)-nocardioazines A and B are reported. The key pyrroloindoline building blocks are rapidly prepared by enantioselective formal [3+2] cycloaddition reactions. The macrocycle of (+)-nocardioazine A is constructed by an unusual intramolecular diketopiperazine formation.
The Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125 (USA) http://reismangroup.caltech.edu.
Haoxuan
H
Wang
Sarah E
SE
Reisman
D000147:Acids, Heterocyclic / Q000737:chemistry*; D001688:Biological Products; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D013237:Stereoisomerism
D000147:Acids, Heterocyclic; D001688:Biological Products
cycloaddition; heterocycles; macrocycles; natural products; total synthesis