Synthesis of trisphaeridine and norchelerythrine through palladium-catalyzed aryl-aryl coupling reaction

被引：101

作者：

Harayama, T ^{[1
]}

Akamatsu, H ^{[1
]}

Okamura, K ^{[1
]}

Miyagoe, T ^{[1
]}

Akiyama, T ^{[1
]}

Abe, H ^{[1
]}

Takeuchi, Y ^{[1
]}

机构：

[1] Okayama Univ, Fac Pharmaceut Sci, Okayama 7008530, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 05期

关键词：

D O I：

10.1039/b008683p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total syntheses of trisphaeridine (3) and norchelerythrine (4), fully aromatized benzo[c]phenanthridine alkaloids, were accomplished via the internal aryl-aryl coupling reaction of halo amides protected by a methoxymethyl group with the palladium reagent, followed by reduction with lithium aluminium hydride and treatment with hydrochloric acid.

引用

页码：523 / 528

页数：6

共 40 条

[1] PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION [J].

AMES, DE ;

OPALKO, A .

TETRAHEDRON, 1984, 40 (10) :1919-1925

[2]

[Anonymous], ALKALOIDS

[3] SYNTHETICAL EXPERIMENTS IN THE CHELIDONINE-SANGUINARINE GROUP OF THE ALKALOIDS .4. [J].

BAILEY, AS ;

WORTHING, CR .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (NOV) :4535-4543

[4] CONVERGENT ROUTES TO THE [1,3]DIOXOLO[4,5-J]PHENANTHRIDIN-6(5H)-ONE AND 2,3,4,4A-TETRAHYDRO[1,3]DIOXOLO[4,5-J]PHENANTHRIDIN-6(5H)-ONE NUCLEI - APPLICATION TO SYNTHESES OF THE AMARYLLIDACEAE ALKALOIDS CRINASIADINE, N-METHYLCRINASIADINE AND TRISPHAERIDINE [J].

BANWELL, MG ;

COWDEN, CJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (12) :2235-2254

[5] OXIDATION DURING REDUCTIVE CYCLIZATIONS USING BU3SNH [J].

BOWMAN, WR ;

HEANEY, H ;

JORDAN, BM .

TETRAHEDRON, 1991, 47 (48) :10119-10128

[6] QUATERNARY BENZO[C]PHENANTHRIDINE ALKALOIDS [J].

DOSTAL, J ;

POTACEK, M .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1990, 55 (12) :2840-2873

[7] SYNTHESIS OF BERBERASTINE [J].

DYKE, SF ;

TILEY, EP .

TETRAHEDRON, 1975, 31 (06) :561-568

[8] INHIBITORS OF DNA TOPOISOMERASE-I ISOLATED FROM THE ROOTS OF ZANTHOXYLUM-NITIDUM [J].

FANG, SD ;

WANG, LK ;

HECHT, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5025-5027

[9] Molecular determinants of site-specific inhibition of human DNA topoisomerase I by fagaronine and ethoxidine - Relation to DNA binding [J].

Fleury, F ;

Sukhanova, A ;

Ianoul, A ;

Devy, J ;

Kudelina, I ;

Duval, O ;

Alix, AJP ;

Jardillier, JC ;

Nabiev, I .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (05) :3501-3509

[10] A versatile synthesis of fully aromatic benzo[c]phenanthridine alkaloids [J].

Geen, GR ;

Mann, IS ;

Mullane, MV ;

McKillop, A .

TETRAHEDRON, 1998, 54 (33) :9875-9894

← 1 2 3 4 →