Enantioselective synthesis of (-)-cis-clavicipitic acid.
An enantioselective synthetic method for (-)-cis-clavicipitic acid (1) was reported. 1 was obtained in 10 steps (99% ee and 20% overall yield) from 1H-indole-3-carboxylic acid methyl ester (9) via asymmetric phase-transfer catalytic alkylation and diastereoselective Pd(II)-catalyzed intramolecular aminocyclization as key steps.
Ku
Jin-Mo
JM
Research Institute of Pharmaceutical Science and College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Jeong
Byeong-Seon
BS
Jew
Sang-sup
SS
Park
Hyeung-geun
HG
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D000478:Alkylation; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D002384:Catalysis; D002967:Claviceps / Q000737:chemistry*; D004876:Ergot Alkaloids; D004952:Esters; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D044367:Phase Transition; D013237:Stereoisomerism
D000470:Alkaloids; D001381:Azepines; D004876:Ergot Alkaloids; D004952:Esters; D007211:Indoles; C524935:clavicipitic acid; C012382:indole-3-carboxylic acid; D010165:Palladium