Highly convergent route to cyclopeptide alkaloids: total synthesis of ziziphine N.
[structure: see text]. A highly convergent protocol to cyclopeptide alkaloids, as demonstrated by the first total synthesis of antiplasmodial agent ziziphine N, is developed. The key elements include construction of its aryl ether unit via Mitsunobu reaction, installation of its enamide part via CuI/N,N-dimethylglycine-catalyzed coupling reaction, and ring closure with coupling agents such as FDDP and DPPA.
He
Gang
G
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, China.
Wang
Jing
J
Ma
Dawei
D
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D010456:Peptides, Cyclic; C519473:ziziphine N