Reductive Pictet-Spengler cyclization of nitriles in the presence of tryptamine: Synthesis of indolo[2,3-a]quinolizidine, nazlinine, and elaeocarpidine

被引：20

作者：

Diker, K ^{[1
]}

ElBiach, K ^{[1
]}

deMaindreville, MD ^{[1
]}

Levy, J ^{[1
]}

机构：

[1] UNIV REIMS,FAC PHARM,CNRS,LAB TRANSFORMAT SYNTH SUBST NAT,F-51096 REIMS,FRANCE

来源：

JOURNAL OF NATURAL PRODUCTS | 1997年 / 60卷 / 08期

关键词：

D O I：

10.1021/np970191s

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Preparation of tetrahydro-beta-carbolines through catalytic hydrogenation of nitriles in the presence of tryptamine was applied to simple syntheses of indolo[2,3-a]quinolizidine (3), nazlinine (4), and elaeocarpidine (7).

引用

页码：791 / 793

页数：3

共 38 条

[1] Reductive Pictet-Spengler cyclization of nitriles in the presence of tryptamine: Synthesis of indolo[2,3-a]quinolizidine, nazlinine, and elaeocarpidine (vol 60, pg 791, 1997)
Diker, K
El Biach, K
de Maindreville, MD
Levy, J
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (06): : 862 - 862
[2] Pictet-spengler synthesis of some new indolo[2,3-c]quinolines
Dabaien, Saida A.
El-Abadelab, Mustafa M.
Haddad, Salim F.
Duddeck, Helmut
HETEROCYCLES, 2007, 71 (04) : 835 - 846
[3] A fast assembly of pentacyclic benz[f]indolo[2,3-a]quinolizidine core by tandem intermolecular formal aza-[3+3] cycloaddition/Pictet-Spengler cyclization:: A formal synthesis of (±)-tangutorine
Luo, SJ
Zhao, JR
Zhai, HB
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (13): : 4548 - 4550
[4] STUDIES ON THE SYNTHESIS OF THE INDOLO[2,3-A]QUINOLIZIDINE SYSTEM
RUBIRALTA, M
DIEZ, A
BOSCH, J
SOLANS, X
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23): : 5591 - 5597
[5] SYNTHESIS OF INDOLO[2,3-A]QUINOLIZIDINE-3-ONE
MANNA, RK
JAISANKAR, P
GIRI, VS
SYNTHETIC COMMUNICATIONS, 1995, 25 (19) : 3027 - 3034
[6] Synthesis of indolo[2,3-a]quinolizine and hexahydro-1H-indolizino[8,7-b]indole derivatives by cascade condensation, cyclization, and Pictet-Spengler reaction: an application to the synthesis of (±)-harmicine
Sanaboina, Chakrapani
Jana, Samaresh
Chidara, Sridhar
Patro, Balaram
Raolji, Gajendrasinh Balvantsinh
Eppakayala, Laxminarayana
TETRAHEDRON LETTERS, 2012, 53 (37) : 5027 - 5029
[7] Asymmetric Synthesis of the Indolo[2,3-α]quinolizine Alkaloid (+)-Cuscutamine via a Diastereoselective Intramolecular Pictet-Spengler Reaction
St Pierre, Max
McNulty, James
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (41)
[8] MODIFICATION OF THE PICTET-SPENGLER REACTION IN THE SYNTHESIS OF FUSED 2,3-BENZODIAZOCINES
Tolkunov, A. S.
Baumer, V. N.
Palamarchuk, G. V.
Shishkin, O. V.
Mazepa, A. V.
Tolkunov, S. V.
Bogza, S. L.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 47 (08) : 1006 - 1013
[9] SYNTHESIS OF CORYNANTHEIDINE ALKALOIDS .2. UNUSUAL EPIMERIZATION OF INDOLO[2,3-A]QUINOLIZIDINE AND BENZO[A]QUINOLIZIDINE DERIVATIVES
BARCZAIBEKE, M
DORNYEI, G
KAJTAR, M
SZANTAY, C
TETRAHEDRON, 1976, 32 (09) : 1019 - 1023
[10] Controlled epimerization of indolo[2,3-a]quinolizidine derivatives:: An efficient total synthesis of (±)-tacamonine
Lounasmaa, M
Karinen, K
Belle, DD
Tolvanen, A
TETRAHEDRON, 1998, 54 (1-2) : 157 - 164

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