Directed ortho metalation -: Cross coupling connections.: Remote lateral metalation -: Cyclization of 2-imino-2′-methyl biaryls to 9-aminophenanthrenes.: A synthesis of the alkaloid piperolactam C

被引：27

作者：

Benesch, L ^{[1
]}

Bury, P ^{[1
]}

Guillaneux, D ^{[1
]}

Houldsworth, S ^{[1
]}

Wang, X ^{[1
]}

Snieckus, V ^{[1
]}

机构：

[1] Univ Waterloo, Guelph Waterloo Ctr Grad Work Chem, Dept Chem, Waterloo, ON N2L 3G1, Canada

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 09期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(97)10670-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Imino-2'-methyl biaryls, conveniently available by Suzuki cross coupling protocol, undergo lithium diethyl amide-mediated metalation - cyclization to give 9-aminophenanthrenes (Table 1). The application of this new general methodology to the first synthesis of the alkaloid piperolactam C (9) is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：961 / 964

页数：4

共 7 条

[1] Synthetic strategies based on combined directed ortho and remote metalation cross coupling reactions. Total synthesis of defucogilvocarcins and piperolactam C.
Snieckus, V
James, CA
Houldsworth, SJ
Benesch, L
Bury, P
Guillaneux, D
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U13 - U13
[2] Directed ortho metalation -: Cross coupling connections.: Total synthesis of Amaryllidaceae alkaloids buflavine and 8-O-demethylbuflavine
Patil, PA
Snieckus, V
TETRAHEDRON LETTERS, 1998, 39 (11) : 1325 - 1326
[3] Combined directed ortho-metalation, remote metalation, and Stille cross-coupling strategies.: Concise stereoselective synthesis of polysubstituted 9H-fluoren-9-ones
Castanet, Anne-Sophie
Tilly, David
Veron, Jean-Baptiste
Samanta, Subhendu S.
De, Asish
Ganguly, Tapan
Mortier, Jacques
TETRAHEDRON, 2008, 64 (15) : 3331 - 3336
[4] Combined directed ortho and remote metalation -: Cross-coupling strategies.: General method for benzo[a]carbazoles and the synthesis of an unnamed indolo[2,3-a]carbazole alkaloid
Cai, XW
Snieckus, V
ORGANIC LETTERS, 2004, 6 (14) : 2293 - 2295
[5] Directed ortho and Remote Metalation -@ Cross Coupling Connections. Buchwald-@Hartwig Synthesis of 2-@Carbamoyl Diarylamines. Regioselective Anionic Routes to Acridones, Oxindoles, Dibenzo-@[b,f]azepinones, and Anthranilate Esters
MacNeil, S. L.
Gray, M.
Briggs, L. E.
Li, J. J.
Synlett, (04):
[6] Directed ortho and remote metalation - Cross coupling connections. Buchwald-Hartwig synthesis of 2-carbamoyl diarylamines. Regioselective anionic routes to acridones, oxindoles, dibenzo-[b,f]azepinones, and anthranilate esters
MacNeil, SL
Gray, M
Briggs, LE
Li, JJ
Snieckus, V
SYNLETT, 1998, (04) : 419 - +
[7] Ortho-directed metalation of 3-carboxy-β-carbolines:: Use of the SmI2-cleavable 9-N-(N′,N′-dimethylsulfamoyl) blocking group for the preparation of 9-N-deprotected 4-amino derivatives via azide introduction or a palladium-catalyzed cross-coupling reaction
Batch, A
Dodd, RH
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03): : 872 - 877

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