Direct olefination at the C-4 position of tryptophan via C-H activation: application to biomimetic synthesis of clavicipitic acid.
The first Pd-catalyzed method for direct olefination at the C4 position of tryptophan derivatives has been developed via C-H activation to prepare 4-substituted tryptophans, which could be used for the synthesis of many hemiterpenoid indole alkaloids. This reaction proceeds under mild reaction conditions and with exceptional tolerance to a variety of functional groups. Furthermore, the efficiency of this method is demonstrated by the rapid and biomimetic synthesis of clavicipitic acid.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China.
Qiang
Q
Liu
Qingjiang
Q
Li
Yongfan
Y
Ma
Yanxing
Y
Jia
D002384:Catalysis; D004876:Ergot Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
D004876:Ergot Alkaloids; C524935:clavicipitic acid; D010165:Palladium; D014364:Tryptophan