Synthesis of Isoindolobenzazepine Alkaloids Based on Radical Reactions or Pd(0)-Catalyzed Reactions

被引：46

作者：

Onozaki, Yu ^{[1
]}

Kurono, Nobuhito ^{[1
]}

Senboku, Hisanori ^{[1
]}

Tokuda, Masao ^{[1
]}

Orito, Kazuhiko ^{[1
]}

机构：

[1] Hokkaido Univ, Organ Synth Lab, Div Mol Chem, Grad Sch Engn, Sapporo, Hokkaido 0608628, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 15期

关键词：

INTRAMOLECULAR HECK REACTION; CONVENIENT SYNTHESIS; TRANSLOCATION REACTIONS; NITROGEN-HETEROCYCLES; AROMATIC-SUBSTITUTION; RING-EXPANSION; ARYL HALIDES; SIMPLE ROUTE; LENNOXAMINE; CYCLIZATION;

D O I：

10.1021/jo900311g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methods for synthesis of a ring system characteristic of isoindolobenzazepine alkaloids were studied. Synthesis of lennoxamine and a formal synthesis of chelenine were accomplished in a short route via radical or Pd(0)-catalyzed cyclization as the key step. An altenative approach based on a radical migration of a cyano group or Pd(0)-catalyzed carbonylation was also developed for both alkaloids.

引用

页码：5486 / 5495

页数：10

共 50 条

[31] Synthesis of Phenanthrene and Alkyl Phenanthrenes by Palladium(0)-Catalyzed Pericyclic Reactions
Jana, Rathin
Biswas, Anup
Samanta, Shubhankar
Ray, Jayanta K.
SYNTHESIS-STUTTGART, 2010, (12): : 2092 - 2100
[32] Heck reactions catalyzed by Pd(0)-PVP nanoparticles under conventional and microwave heating
Martins, Daniela de L.
Alvarez, Heiddy M.
Aguiar, Lucia C. S.
Antunes, Octavio A. C.
APPLIED CATALYSIS A-GENERAL, 2011, 408 (1-2) : 47 - 53
[33] Synthesis of cystothiazole E and formal syntheses of cystothiazoles A and C by Pd0-catalyzed cross-coupling reactions
Bach, T
Heuser, S
CHEMISTRY-A EUROPEAN JOURNAL, 2002, 8 (24) : 5585 - 5592
[34] Synthesis of novel rigid analogs of tryptamine as potential serotonin ligands through Pd(0)-catalyzed diaryl coupling reactions
Kambhampati, Ramasastri
Kothmirkar, Prabhakar
Deshpande, Amol D.
Arepalli, Sobhanadri
Karturi, Kameswara Rao
Pamuleti, Narasimha Reddy G.
Shinde, Anil K.
Nirogi, Ramakrishna V. S.
SYNTHETIC COMMUNICATIONS, 2008, 38 (14) : 2419 - 2428
[35] Pd(0)-Catalyzed radical aryldifluoromethylation of activated alkenes
Wang, Jian-Yong
Su, Yi-Ming
Yin, Feng
Bao, Yan
Zhang, Xin
Xu, Yue-Ming
Wang, Xi-Sheng
CHEMICAL COMMUNICATIONS, 2014, 50 (31) : 4108 - 4111
[36] Pd(0) or Pd(II)-catalyzed ring-opening reactions of benzylidene- and alkylidenecyclopropyl ketones and aldehydes
Tang, Xiang-Ying
Shi, Min
TETRAHEDRON, 2009, 65 (43) : 8863 - 8868
[37] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions
Amatore, C
Jutand, A
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) : 314 - 321
[38] INTRAMOLECULAR RADICAL CYCLIZATION REACTIONS - AN APPROACH TO THE INDOLE ALKALOIDS
DITTAMI, JP
RAMANATHAN, H
TETRAHEDRON LETTERS, 1988, 29 (01) : 45 - 48
[39] Radical translocation reactions in synthesis
Robertson, J
Pillai, J
Lush, RK
CHEMICAL SOCIETY REVIEWS, 2001, 30 (02) : 94 - 103
[40] Pd(II)- and Pd(0)-cocatalyzed reactions of sulfonamides with MCPs
Shi, M
Chen, Y
Xu, B
ORGANIC LETTERS, 2003, 5 (08) : 1225 - 1228

← 1 2 3 4 5 →