Synthesis of benzo[c]phenanthridine alkaloids, chelerythrine and nitidine, using a novel palladium-phosphine combination system -Pd(OAc)2, DPPP, and Bu3P-

被引：13

作者：

Harayama, T ^{[1
]}

Akiyama, T ^{[1
]}

Nakano, Y ^{[1
]}

Shibaike, K ^{[1
]}

机构：

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

来源：

HETEROCYCLES | 1998年 / 48卷 / 10期

关键词：

D O I：

10.3987/COM-98-8284

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of chelerythrine (1) and nitidine (4) was accomplished via the aryl-aryl cyclization reaction using a novel Pd reagent prepared from Pd(OAc)(2), DPPP, and Bu3P. The present method was very versatile for coupling reaction not only between aromatic triflate and arene but also between aromatic halide and arene.

引用

页码：1989 / 1992

页数：4

共 27 条

[1]

[Anonymous], ALKALOIDS

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

DOSTAL, J ;

POTACEK, M .

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

[3] 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

[4] A versatile synthesis of benzo[c]phenanthridine alkaloids [J].

Geen, GR ;

Mann, IS ;

Mullane, MV ;

McKillop, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (14) :1647-1648

[5]

HANAOKA M, 1987, CHEM PHARM BULL, V35, P2348

[6] CHEMICAL TRANSFORMATION OF PROTOBERBERINES .9. A BIOMIMETIC SYNTHESIS OF OXYCHELERYTHRINE, DIHYDROCHELERYTHRINE, AND CHELERYTHRINE FROM BERBERINE [J].

HANAOKA, M ;

MOTONISHI, T ;

MUKAI, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12) :2253-2256

[7]

Harayama T, 1996, CHEM PHARM BULL, V44, P1634

[8]

Harayama T, 1997, CHEM PHARM BULL, V45, P1723

[9]

HERERT JM, 1990, BIOPHYS RES COMMUN, V172, P993

[10]

ISHII H, 1992, CHEM PHARM BULL, V40, P1770, DOI 10.1248/cpb.40.1770

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