The Diels-Alder reactions of quinone imine ketals: A synthesis of the ergot skeleton

被引：0

作者：

Banfield, SC ^{[1
]}

Kerr, MA ^{[1
]}

机构：

[1] Univ Western Ontario, Dept Chem, London, ON N6A 5B7, Canada

来源：

SYNLETT | 2001年 / 03期

关键词：

Diels-Alder reactions; quinones; alkaloids; cycloadditions;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The high pressure (13 kbar) Diels-Alder reaction of N-benzoyl-p-benzoquinone-mono-imine dimethyl ketal with an appropriate diene yields, after treatment with anhydrous acid, a dihydronaphthanilide, Conversion to the tricyclic skeleton of the ergot alkaloids is effected via a series of simple transformations.

引用

页码：436 / 438

页数：3

共 12 条

[1] PALLADIUM-CATALYZED TRIETHYLAMMONIUM FORMATE REDUCTION OF ARYL TRIFLATES - A SELECTIVE METHOD FOR THE DEOXYGENATION OF PHENOLS [J].

CACCHI, S ;

CIATTINI, PG ;

MORERA, E ;

ORTAR, G .

TETRAHEDRON LETTERS, 1986, 27 (45) :5541-5544

[2]

KERR MA, 1995, SYNLETT, P1165

[3]

KERR MA, 1996, SYNLETT, P897

[4] Reductions of aryl perfluorosulfonates with dimethylamine•borane (Me2NH•BH3) catalyzed by Pd(0):: an operationally simple, inexpensive, and general protocol [J].

Lipshutz, BH ;

Buzard, DJ ;

Vivian, RW .

TETRAHEDRON LETTERS, 1999, 40 (38) :6871-6874

[5]

NINOMIYA I, 1975, ALKALOIDS, V15, pCH1

[6]

NINOMIYA I, 1990, ALKALOIDS, V38, pCH1

[7] PALLADIUM CATALYZED REDUCTION OF ARYL TRIFLATES - UTILIZATION IN THE SYNTHESIS OF ANGELICIN, OLIVIN AND CHROMOMYCINONE FROM PHENOLS PRODUCED IN THE BENZANNULATION REACTION OF CHROMIUM CARBENE COMPLEXES [J].

PETERSON, GA ;

KUNNG, FA ;

MCCALLUM, JS ;

WULFF, WD .

TETRAHEDRON LETTERS, 1987, 28 (13) :1381-1384

[8]

PROTIVA M, 1985, J COLLECT CZECH CHEM, V50, P1888

[9]

STOLL A, 1965, ALKALOIDS, V8, pCH21

[10] THE CHEMISTRY OF ACYLATED QUINONE IMINE KETALS - NUCLEOPHILIC AND ORGANOLITHIUM ADDITION-REACTIONS [J].

SWENTON, JS ;

BONKE, BR ;

CLARK, WM ;

CHEN, CP ;

MARTIN, KV .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2027-2034

← 1 2 →