Efficient total synthesis of (-)-cis-clavicipitic acid.
An efficient total synthesis of (-)-cis-clavicipitic acid has been achieved in seven linear steps (42% overall yield) from the known compound 6. The present synthesis features a palladium-catalyzed indole synthesis to provide the optically pure 4-chlorotryptophan derivative and a Heck reaction using aryl chloride as partner. It has also been discovered that the key azepinoindole nucleus could be stereoselectively constructed via a Mg(ClO(4))(2)-mediated intramolecular aminocyclization.
Xu
Zhengren
Z
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, China.
Li
Qingjiang
Q
Zhang
Lihe
L
Jia
Yanxing
Y
D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002712:Chlorides / Q000737:chemistry; D003500:Cyclization; D015195:Drug Design; D004876:Ergot Alkaloids; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D001381:Azepines; D002712:Chlorides; D004876:Ergot Alkaloids; D007211:Indoles; C524935:clavicipitic acid; D010165:Palladium