Photodecarboxylative benzylation of N-alkylphthalimides:: A concise route to the aristolactam skeleton

被引：39

作者：

Griesbeck, AG

Warzecha, KD

Neudöfl, JM

Görner, H

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

[2] Max Planck Inst Bioanorgan Chem, D-45413 Mulheim, Germany

来源：

SYNLETT | 2004年 / 13期

关键词：

electron transfer; photochemistry; radical reactions; eliminations; aristolactam alkaloids;

D O I：

10.1055/s-2004-832850

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photoinitiated metal-free benzylation of N-alkyl phthalimides with arylacetates in aqueous solution followed by acid-catalyzed dehydration serves as a convenient route to methoxy-substituted precursors to phenanthrene lactam alkaloids.

引用

页码：2347 / 2350

页数：4

共 18 条

[1] Aristolochic acid as a probable human cancer hazard in herbal remedies: a review [J].

Arlt, VM ;

Stiborova, M ;

Schmeiser, HH .

MUTAGENESIS, 2002, 17 (04) :265-277

[2]

CEPHARANONE A, 1997, SYNLETT, P1475

[3] A new aristolactam alkaloid and anti-platelet aggregation constituents from Piper taiwanense [J].

Chen, YC ;

Chen, JJ ;

Chang, YL ;

Teng, CM ;

Lin, WY ;

Wu, CC ;

Chen, IS .

PLANTA MEDICA, 2004, 70 (02) :174-177

[4] Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii [J].

Chia, YC ;

Chang, FR ;

Teng, CM ;

Wu, YC .

JOURNAL OF NATURAL PRODUCTS, 2000, 63 (08) :1160-1163

[5] Structure-activity relationships in a series of bisquaternary bisphthalimidine derivatives modulating the muscarinic M2-receptor allosterically [J].

Cid, HMB ;

Tränkle, C ;

Baumann, K ;

Pick, R ;

Mies-Klomfass, E ;

Kostenis, E ;

Mohr, K ;

Holzgrabe, U .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (11) :2155-2164

[6] An efficient one-pot synthesis of 3-(aryl and alkyl)methylene-1H-isoindolin-1-ones via aryne cyclization and Horner reaction of o- (and m-)halogeno-N-phosphorylmethylbenzamide derivatives. [J].

Couture, A ;

Deniau, E ;

Grandclaudon, P .

TETRAHEDRON, 1997, 53 (30) :10313-10330

[7] PHOTOCHEMISTRY OF N-PHTHALOYL DERIVATIVES OF ELECTRON-DONOR-SUBSTITUTED AMINO-ACIDS [J].

GRIESBECK, AG ;

HENZ, A ;

HIRT, J ;

PTATSCHEK, V ;

ENGEL, T ;

LOFFLER, D ;

SCHNEIDER, FW .

TETRAHEDRON, 1994, 50 (03) :701-714

[8] Laser flash photolysis study of N-alkylated phthalimides [J].

Griesbeck, AG ;

Görner, H .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1999, 129 (03) :111-119

[9]

Griesbeck AG, 2000, SYNLETT, P1455

[10]

Griesbeck AG, 1999, SYNLETT, P492

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