Total Synthesis of (+)-Lysergic Acid

被引：67
作者：
Liu, Qiang [1 ,2 ]
Jia, Yanxing [1 ,2 ]
机构：
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, 38 Xueyuan Rd, Beijing 100191, Peoples R China
[2] Jiangxi Sci & Technol Normal Univ, Jiangxi Key Lab Organ Chem, Nanchang 330013, Peoples R China
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 18期
基金：
中国国家自然科学基金;
关键词：
RING-CLOSING METATHESIS; EFFICIENT TOTAL-SYNTHESIS; SUZUKI-MIYAURA REACTION; FORMAL TOTAL-SYNTHESIS; LYSERGIC-ACID; (+/-)-LYSERGIC ACID; ERGOT ALKALOIDS; (&/-)-LYSERGIC ACID; DIRECT ANNULATION; CHLOROPEPTIN-I;
D O I：
10.1021/ol2018467
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A stereocontrolled total synthesis of (+)-lysergic acid (1) is achieved using three metal-catalyzed methodologies for the construction of three key rings. Highlights of the synthesis include Pd-catalyzed indole synthesis to form the Bring, a RCM reaction to form the D ring, and an intramolecular Heck reaction to form the C ring.
引用
收藏
页码：4810 / 4813
页数：4
相关论文
共 64 条
[1]   INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].
ABELMAN, MM ;
OH, T ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4130-4133
[2]  
[Anonymous], 1996, MERCK IND, P231
[3]   2 SYNTHESES OF PINANE THROMBOXANE-A2 [J].
ANSELL, MF ;
CATON, MPL ;
STUTTLE, KAJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :1069-1077
[4]  
ARMSTRONG VW, 1976, TETRAHEDRON LETT, P4311
[5]   Synthesis and biological activity of 4-amino-7-oxo-substituted analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid [J].
Borrell, JI ;
Teixidó, J ;
Martínez-Teipel, B ;
Matallana, JL ;
Copete, MT ;
Llimargas, A ;
García, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (18) :3539-3545
[6]   A CONCISE, PALLADIUM-CATALYZED APPROACH TO (+/-)-LYSERGIC ACID [J].
CACCHI, S ;
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1988, 29 (25) :3117-3120
[7]   Formation of medium-ring heterocycles by diene and enyne metathesis [J].
Chattopadhyay, Shital K. ;
Karmakar, Swastik ;
Biswas, Titas ;
Majumdar, K. C. ;
Rahaman, H. ;
Roy, B. .
TETRAHEDRON, 2007, 63 (19) :3919-3952
[8]   Intramolecular conjugate displacement:: A general route to hexahydroquinolizines, hexahydroindolizines, and related [m,n,0]-bicyclic structures with nitrogen at a bridgehead [J].
Clive, Derrick L. J. ;
Li, Zhiyong ;
Yu, Maolin .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15) :5608-5617
[9]   Olerin metathesis of amine-containing systems: Beyond the current consensus [J].
Compain, Philippe .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) :1829-1846
[10]   Enantioselective Synthesis of (+)-Isolysergol via Ring-Closing Metathesis [J].
Deck, Jason A. ;
Martin, Stephen F. .
ORGANIC LETTERS, 2010, 12 (11) :2610-2613
1234567